DEAR DR. NERDLOVE: I am a 35 years old man who recently broke up with his girlfriend for 3 years, because I couldn’t handle the fact that she has had several lovers before me and I was an inexperienced virgin. I keep comparing us on that and I feel awful.

My life is severely messed up due to family problems and as a result I have always been alone, feeling disappointed and with low self-esteem. I abstained from coming close to women. I met her through common friends.

She really loves me and I know I would have stayed with her, if it wasn’t for my constant urge to meet and have sex with other girls as I have never done before and “bridge the experience gap”. I never cheated on her and neither did she have a problem with me being inexperienced.

I feel I have lost my one and only precious love with whom I would like to spend the rest of my life. How can I proceed, feel good with myself and come back to her after all? I know from her own words that for the time being she is still there for me, showing her true love. Can I make it or do I have to cope with her loss to truly find myself and “grow up”, finding love with a new mate?

The thoughts that I am old, I don’t have many chances to settle down and that there will always be an abyss of experience separating me from the girls around my age buzz in my head and drive me mad.

Thank you very much in advance!

Virgin In The Wild

DEAR VIRGIN IN THE WILD: I get letters like yours all the time, VitW. Every time it’s someone who feels like there’s a window closing and that if they don’t somehow make up for their utter lack of experience, they’re doomed to never date, ever. When they do find someone, they then get anxious over the difference in numbers; they feel as though that their lack of experience means that either they are “missing out” somehow or that they need to balance out the scales so that they’re more equal with their partner, somehow.

Not that anyone can explain what equality is supposed to bring, exactly.

Here’s a truth: your experience – or lack thereof – isn’t the problem. Your problem is the importance you’re putting on it. The number of partners you’ve had is ultimately meaningless; it doesn’t mean anything other than “you slept with X many people”. It doesn’t automatically mean that you’re a more desirable person; people have sex for reasons that have nothing to do with the person they’re banging. It doesn’t mean that you’re a better lover; people can have lots of one-night stands because they’re selfish dicks who never get a return engagement. It doesn’t mean that you did anything right or wrong or anything else.

Here’s another truth: there is no amount of sex that’s going to be “enough”. When you’re trying to derive your value through how many people you’ve slept with – especially when it’s in comparison with how many people your partner has slept with – then all that’s going to happen is that you’re going to (maybe) rack up notches on your bedpost and still feel empty and unfulfilled. You’ll be trying to fill a bottomless hole with sex and wondering why you never feel any better about it.

The “experience gap” you’re worried about isn’t relevant. If someone is going to judge you based on how many people you have or haven’t slept with, then they are someone you don’t want to be in a relationship with. Someone who’s right for you is someone who accepts the number of partners you’ve had – whether it’s 0, 1 or 100 – as just part of who you are. There will always be people who’ve had more sex than you; that’s ultimately a null value set because it has nothing to do with you.

Being with someone who’s had more sex than you doesn’t mean that they’re judging you and thinking “man if only I had someone who actually had more than me.” It means that they have chosen you. You can either trust your partner and accept that they’re telling you the truth when they tell you that they want to be with you… or you move on.

And you, VitW, can’t seem to accept someone at their word.

Now it’s time for the Chair Leg of Truth: right now, you can’t go back to your ex. I’m sorry, but doing that is just going to destroy any chances you have of actually making that relationship work. One of the things I always tell people who want to know whether they should get back with their ex is that if you haven’t resolved the reasons why you broke up in the first place, you’re just going to replay your break up the second time around. Second verse, same as the first, a little bit louder and a whole lot worse. And you, VitW, have yet to deal with what broke you up.

You don’t need a loudmouth with a blog, my dude. You need a therapist. You need to find someone who can help you pick apart these issues and give you the tools to get your head on right. Until you do that, trying to rekindle your relationship with your ex is just going to cause more pain. If you don’t know where to find a therapist in your area, then you may want to start with the American Association of Sexuality Educators, Counselors and Therapists and find someone to your area.

I’m sorry that you’re hurting, my dude. But you need to address that pain before you try to date again. It’s the only way things are going to get better.

Good luck.

DEAR DR. NERDLOVE: I’m having issues with my love life. As much as I want to, I can’t help but feel like there’s something wrong with me that’s holding me back. When I was younger it was a competition between my mates on who could get more numbers/hookups/dates. So… I put a lot of time and effort into it… And have had a fair few long term relationships (OK not really, the longest was 3 months), but so many hookups and flings. I would like to see them again or more but we make out/do stuff/have sex for a week.. Two weeks and then it fizzles out for some reason.

I do the swipe right on everyone on tinder so I have 767 matches… Don’t get replies all the time I guess a lot of the girls I talk too don’t take it all that seriously. Erm.. Had a really good “copy pasta” message for OkCupid and Plenty of Fish, anyway that’s besides the point. Over the past 6 years that I graduated high school I’ve gone on something like over 1000 dates (yes I realize that sounds partly vain/sad/unbelievable and believe me I wish it weren’t the case). 

SOMETHING ALWAYS GOES WRONG!! Of the last 3 girls I was talking too, I’m mates with one of their exes, one blew off our date and stopped replying (happens fairly often) and I err kind of got irritated and blocked one because I thought she was leading me on (She wasn’t. I’m not prone to this kind of behavior but it does happen every once in awhile, was much more common when I was younger).

I dunno what I’m doing wrong, mate. I’ve always had really low self esteem and thought I was ugly. It doesn’t make sense because I model for a living? (Like fitness/fashion/pageant); I don’t have 6 pack abs… But I’m reasonably fit I think. 

I have a physical disability, and I think it also contributes to my self esteem issues and depression and anxiety issues. I just really identified with what you said; thinking “I have chemistry with everyone who gives me a chance” and the mindset of thinking “women have all the advantages in the dating field”. 

I also seem to have issues with narcissism and ego problems. It’s hard to explain; like I used to get super butthurt when women didn’t reply on fb messenger or something silly like that. I don’t anymore because I’ve seen my exes inboxes and how many nonsense messages something could get lost in or whatever.

Could my attitude towards women be bleeding into my interactions with them?

Rational and obvious thought says nobody is owed sex and you are not entitled to dating someone, or their time. Nor is it a “needed” component of life. I just find myself super lonely without it, wondering and being jealous of all my friends who are in long term relationships.. 

And I find myself feeling like I’m singled out and victimized, even though that’s completely out of left field. I mean it’d have to be one massive conspiracy to specifically target me out of everyone else in the world so that’s totally silly, but yet it’s how I feel.

I’m just tired of being alone. I don’t want to take the stupid red pill anymore or have angry poisonous beliefs about women or “alphas and betas”; yet all I can think about is “I’m ugly, and the good looking guys are the one’s who have all the luck. Stupid douchebags with 6 pack abs! Rawr Anger! Stupid women for wanting to go out with attractive men!”

That was a heavily over dramatic version buuuuut.. I think you can understand the gist of what I feel? 

I don’t want to end up alone. Maybe I should get a kitten or something?

– Guy who thinks he’s ugly but is probably just woefully average

DEAR GUY:Um, my dude, I think you need to look back over what you just wrote to me. You mention feeling as though that having a physical handicap gives you a disadvantage and that you’re unattractive in one paragraph, and in the other mention that you’ve had multiple hook-ups, flings and literally hundreds of matches on Tinder.

And then we’re back to the idea that you’re beta and ugly.

To quote the sage: “You keep using that word. I do no think it means what you think it means.”

So straight talk: yes, your attitude is bleeding out into your interactions with women. However you may feel about your looks, you clearly have enough going on that you’re able to get that initial interest, even dates and hook-ups. But the reason you can’t keep them is because, frankly, you’re a hot mess and women can tell.

You’ve got a real gumbo of issues here, dude. Let’s start with “SOMETHING ALWAYS GOES WRONG.” Of the examples you’ve given, one of them is just basic bad luck. Hey, you’ve got a friend in common and she’s decided that means she can’t date you. That sucks but hey, sh-t happens, wear a hat. You can’t control for bad luck, you can only roll with it and try agian.

The other two are, frankly, your fault. Yeah, some women will just up and ghost a dude and it blows, but if it’s happening to you frequently, then you need to take a moment to stop and do some serious examination about what all those experiences have in common. And frankly, the biggest common denominator those interactions have is… you. You’re dripping a lot of bitterness and entitlement here, man, and that’s in a letter to me. Trust me when I tell you, you are not hiding that from the women you’re talking to. Women are going to pick up on your attitude and decide they’d really rather just cut off communication and get back in the dating pool instead of dealing with you.

Now don’t get me wrong here: I get that you’re frustrated. I totally understand. Back in my bad old days, I was single more often than not and bitter with it. And trust me, that bitterness really drove people away. It’s not just being Eeyore, it’s being the dude who says “yeah I know, I’m ugly and also f

k you for dating someone else”. That alone is going to push people away. But then there’s also the way you’ve described your interactions with people. Getting pissy with someone because you suspect they’re leading them on? That’s not cool. Neither is treating dating as “I want to fit someone into the hole marked ‘girlfriend’ and I don’t care who.” People in relationships want to feel special and desired because they’re them and you want them specifically. If you’re making them feel as though their primary value to you is a warm body, they’re gonna NEXT you so hard your head will spin. Having competitions with your buds about who could get more hook-ups is part and parcel of the whole problem; it dehumanizes women to just being points in a screwed up contest. Yeah, I did that shit too back when I was a PUA; it was gross when I was doing it and it was gross when you were doing it. No woman out there, even those who dig no-strings sex with Johnny Rando, appreciates feeling like they’re an interchangeable cog.

Like Virgin In the Wild up there, you’ve got an attitude problem and a validation problem, not an issue with your looks. You’re trying to use women as proof that you’re not “ugly” or undesirable or what-not and that’s simply never going to work. That’s the bad news.

The good news is, like VitW, you’re recognizing that this is a screweded up situation and you need to change. That’s an important first step, man; you really can’t fix a problem until you recognize that you have a problem. And – more importantly – you’re picking up on the right problem that you need to fix. A lot of people never even get that far.

No amount of external evidence – up to and including that apparently you work AS A MODEL – is going to shut up that voice in your head if you’re relying solely on external validation for your sense of value. You need to learn to find your own value if you want to quit feeling like you don’t measure up to whatever unbelievable standard you seem to have given yourself. And much like I told VitW, the best thing you can do right now is talk to a therapist; working with a mental health professional will go a long way towards unpacking these issues and helping you move towards a more equitable relationship with a person instead of a cardboard cutout with “girlfriend” scrawled across it.

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com)

DEAR DR. NERDLOVE: I’ve had an occasional history of depression and anxiety, and in the last few weeks, these feelings have become a lot more common. I’m a 26 year old virgin who’s never had a girlfriend, so I want to improve socially to the point where I can eventually get married. However, I’m a college student who works two part time jobs, and much of my time will be devoted to this, as well as preparing myself for a future career. I did read your book New Game +, which has lots of information, and while I want to improve socially, I’ve got a very busy schedule.

The problem is, however, outside of my family, I don’t have much of a support network of friends. I moved to where I live three years ago, and I’ve met people here and there, but we’ve largely lost contact. Part of it’s because I’ve been busy with college and work, part is because they’re not as much my personality type, and I live about half an hour away from most of them. I will start seeing a therapist soon, and plan on joining a few MeetUp groups. However, when seeing people around my age who are in a relationship, I get nervous and jealous, and it negatively affects my mood, reminding me of what I don’t have. There are young couples in quite a few of these Meetup groups, and I don’t want this to affect me from going out.

I’m also worried about even after I get help, my depression and anxiety will flare up at the worst possible time, thus negatively affecting my social life and potential romantic prospects. I’ve had things like this happen in the past, which has, needless to say, led to some very awkward moments.

I’ve just got so much on my plate and on my mind, and any help would be appreciated.

Overwhelmed

DEAR OVERWHELMED: First of all, I’m proud of you for the steps you’ve been taking. You’re doing everything right – both to improve your social life and also to address your anxiety and depression. One thing I want you to keep in mind: there are many ways to treat anxiety and depression, and some will work better for you than others will. Remember: the ones that work for you are the ones that work for you, regardless of what form it ends up taking. If your therapist recommends any medication, this isn’t a sign that you’re a failure or someone who couldn’t muscle their way through it. All it means is that this is a therapy they think may work best for you. Many forms of chronic depression and anxiety are chemical in origin; the right medication can help correct this. As someone who’s been on Zoloft, I can tell you: it can absolutely make a difference for you.

And while it’s no substitute for working with a trained therapist, I’m also a fan of learning how to control your own mind as a supplement to whatever else you do. Yoga and meditation may sound crunchy and new-age-y, but they really can be a great way of taking control of your brain when it tries to gallop out of control.

But don’t forget: while many forms of treatment DO take time to take effect, don’t ever be afraid to advocate for your own needs while you’re working with your therapist. If they recommend medication and you have side-effects that make things harder, you have the right to tell them you’d rather try something else.

Now, let’s talk a little about managing those anxieties while you’re building your new social life. The envy you feel around happy couples is understandable; they have something you wish you had after all. However, the mistake is letting that sense of “but why not me?” take over and leave you feeling bitter and resentful. That’s a mindset that can leave you even more lonely than before – and end up cutting you off from potential friends and potential lovers in turn. After all, while they may have something that you wish you did, new friends may well be the people to introduce you to single people who want to date you.

So how do you get around this? Start with noting and naming your feelings. Words have power after all, and the stories you tell yourself become part of how you actually feel. So rather than describing yourself as being envious, observe your feelings. “Huh… I guess I feel envious of that couple over there.”

Notice very carefully that I phrased that as “I FEEL envious”, not “I AM envious”. The latter defines envy as an integral part of who you are – envy is a core to your identity. The other describes a feeling, and one that’s temporary at that. Not only does this create a layer of abstraction between you and those negative feelings, but it reinforces your control over them. You’re reminding yourself that feeling a particular way is an option, not destiny.

Once you’ve noted and named those feelings, then reframe them. The fact that there are young couples out there doesn’t take anything away from you; neither of them represents a loss to you. What they do represent is that love is real and out there, and if they can find it, then so can you. In a very real way, that love means “hope”.

As weird as it may sound, telling yourself that you’re actually happy for them helps you on the rebound. In a very real way, attitude is destiny; a positive outlook on life makes you more successful in everything that you do. Having a positive attitude and outlook makes you more emotionally resilient. You may fail at times – and that’s fine – those failures are something that you can learn from. They’re something you can bounce back from and – importantly – overcome. And having a positive outlook, particularly when it comes to socializing, makes you more popular. People don’t like spending time around negative people. But the guy who’s generally cheerful and upbeat, even if he’s still striving for the things he wants? That guy is going to be pretty popular. Attitudes are contagious, after all and people feel better around positive folks. That, in turn, makes them want to spend more time with those same people.

So yeah, you may feel a little weird and uncomfortable around them at first. But the more you reframe the situation – that they’re proof that what you want is out there and attainable – then they go from being a negative to a positive. They’re not your opponents, as it were, but aspirational figures. Relationship goals, as it were.

Plus, as an added bonus: seeing couples in happy and successful relationships also provide role models for how relationships can work. Obviously not every relationship style is going to work for you, and every relationship is going to have it’s quirks. But being able to look around and see how other people make it work can give you an idea of how things can work for you, too.

Oh, and one more thing: even under treatment, you can have flare-ups of anxiety and depression. I still have times when my depression weighs pretty heavily on me. But having worked with therapists and learned my own triggers, I know how to handle them. As you work through your own treatments, you’ll find the things that work for you too. And while you may have those moments when everything is dark, poison arrows fall from the sky and the pillars of heaven shake, you’ll be able to look it square in the eye and say “Bring it on. I can take it.”

It seems like a lot, but you’re strong and you’re on the right path. You’ve got this, Overwhelmed.

All will be well.

Good luck.

DEAR DR. NERDLOVE: Some people are natural artists and end up in the Louvre next to the Mona Lisa. Others end up with glitter, crazy paint and spaghetti noodles and still create abominations. It’s the same for me and dating, I read you and a few other awesome blogs to try and upgrade my skill set. I do a pretty good human impression but I have this one terrible quality: creepers and abusers are magnetically drawn to me and please for the love of gods, teach me how not to be the approachable gal! I’ve tried headphones, strategically place books and endless hours of cats or archaeology…

I gave up on being nice and accommodating a long time ago but I do have a very wide circle of friends with various quirks and issues. I’ve been slowly removing the Nopes: the missing stairs, creepers and boundary toe-stompers from my circle (like the large guy who was going to kidnap and assault me in his unregistered car “as a joke” that caused me to have a nervous breakdown and have to leave university for the semester). What’s worse is teaching people around me about rape culture like my mum who has no boundaries and just doesn’t get why guys swooping in to save you against your will (even if they are your older professor friends is creepy and gross). My family is screwed up but loving that’s a whole other letter, Doc.

Me trying everything from dressing modestly to resting bitch face and headphones everywhere, it doesn’t stop me from being stalked by men and women alike (everything from a random local community dude creep, to a girl cyber stalking me in a uni class to do her work and then creepy abusive guy I most recently dated for 3 months but ended things hard is now using mutual hobbies as a way of seeing me, so I quit gaming and advertising where I’ll be until after I’ve been there). Pre last creeper, I had to live cautiously and hide my existence and I was only just recovering my sense of safety and freedom when he turned out to be gross.

Last creepy guy sabotaged my academic work, ignored me for 8-10 hour online games, outrageously lied and stole from me to leverage his way back into my life, abused me and gaslit me, had weird kinks he wouldn’t negotiate until mid coitus, left sh*t stains on my sheets that I initially thought were one of my cats having been sick, thought cutting finger nails and reciprocal foreplay was not a thing he had the do, and then threatened suicide when he wouldn’t get his own way. My housemate years ago was found dead by me so I really didn’t want to come home to his bloated corpse in my cute little flat.

I’ve tried all the no contact and blocking to the sun with this last disgusting guy and victim support counseling because the stress brought back my OCD since that guy was a hoarder and had a stench like a dying whale and rotten teeth. I’m addicted to sniffing mothballs, listening to T-Swift’s “Clean”, I just got 5 bottles of perfume for my birthday and I’ve just stopped washing my hands 34 times a day. But I missed gaming and the friends I made in it.

So, I personally engaged actual qualified professionals help to negotiate my return to our role playing club and other gaming hobbies (think two personal psychologist sessions especially devoted and victim support counseling to coming back) and our gaming group wanted us to go through *mediation* without specifying what it was they wanted of me and he has done nothing to talk to them so I left the hobby altogether because they had no victim support policy and didn’t enforce any consequences on him and they wouldn’t ban him from games despite his refusal to talk at the table.

I’m not being part of a club that pushes me out and expects me to do all the mature compromising at my expense for this creepy dude. The thing is, this guy was deemed unsafe by Team Me, but he hogs all the games and there’s no effing justice so I miss out on everything in case he is there, can’t create or confirm plans because he shows up uninvited and I have to avoid a lot of cool things I’d like to do in case he’s there. Leaving gaming was one thing, but I’m tired of missing out on medieval faires or games, the free comic days or the cons in my city or geek themed pub quizzes.

So what do I do to keep away the creepers like this one and since I’ve emerged from my rock, what do I do if I see this guy? I already have mental health disabilities and he makes me both anxious and full of rage. I have taken up poetry and improv since and now I’m going back to university to study in July after the breakdown.

Life On Mars

DEAR LIFE ON MARS: I’m sorry all that happened to you, LoM. You’ve done a lot of things right – from kicking the guy to the curb, to focusing on your self-care and doing what you need to do to be healthy and safe.

Now, let’s dig in a little to what you can do next – both in dealing with this guy, with your former social groups and avoiding future creepers.

First and foremost: boundaries, boundaries, boundaries. You have the right to enforce your boundaries at all times, to any degree that you wish and by god you should do so. Establishing firm boundaries – including a willingness to call dudes out on their bad behavior you’re being irrational, right then and there – is part of how you keep creepers and predators out of your life. Yeah, it’s scary and intimidating. There will be guys – and their (occasionally even well-meaning) enablers – who will push back against you for having boundaries or enforcing  them. They will tell you that . Well, a) f-ck that and b) you’ve had enough bad experiences that your Spidey-sense is going to be more sensitive than others’. They will tell you that it’s unfair because he doesn’t mean it or know better. Tough, because it’s pretty easy to see when a dude only behaves like that to women and anyway even goldfish can learn. They will say you’re being a bitch. Fine. BE a bitch. Be Queen Bitch, First of Her Name, Empress of Back Off Or Pull Back a Stump.

Being “nice” is great, but “nice” also is what a—-holes will leverage to get to you. Sometimes you’ve got to be a mean motherf-cking soldier of love guarding your own security. You’ve been hurt, abused and violated by people before. You have to be the strongest advocate of your own safety and interests. So put up those boundaries, and let the people who’re worth letting in prove it by respecting them.

Next: your social circle. Unfortunately, y’all got a bad case of Missing Stair paired with an equally bad case of Geek Social Fallacies. A lot of geek communities are averse to “drama”. Unfortunately, they tend to blame said drama on the person who points out that it exists, not the person causing it. It’s easier to pretend it doesn’t happen than it is to actually address it and admit that maybe the person they like is a creeper and they need to do something about it. It’s easier to get the person saying “we have a problem” to be quiet about it than it is to actually do something.

Now, you can consider approaching some of the members of your old group individually and giving them the download on what this dude has done. Taking this on a one-on-one level might get people to listen in a way that a group setting might not, especially if there’re many, drama-enabling “Let us REASON together” who drown out all other voices. It may be easier to divide and conquer and keep those individual friendships even if you can’t be with the entire group. And hey… get enough of those together and you’ve got a new group entirely. But if they, as a whole, are going to focus on the idea that there’s some middle-ground to be had… well, I refer you back to the Boundaries Boundaries Boundaries paragraph.

And, bee-tee-dubs: boundaries also means “tell me if this dude is going to be at the event too” or saying “I can’t be at this event if he is going to be there”. Yeah, you’re asking them to draw lines and choose sides. Which sucks, but your right to protect yourself overrides “be reasonable”.

And finally: if you do have friends you can go to Faire with or cons or pub-quizzes, do so. Let them be your shield, your linebacker, your tank. They can run interference if homeboy sees you and tries to make contact. They can be the ones to get you out of the room if you start to have a panic attack or need to get out before he triggers some form of PTSD. Don’t think #squadgoals, think #brutesquad.

It sucks that sometimes assholes win. But if you want to continue enjoying the hobbies you love and the others won’t consider safety over Social Fallacies, you may have to carve out your own space instead.

Good luck.

Dr. Nerdlove is not a real doctor. Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com)

DEAR DR. NERDLOVE: I just recently turned 27, and have yet to have an actual relationship. I often worry that the place I’m currently at in life makes me undateable: I just transferred from a community college to a university, and I still have a couple of years of undergrad to go.

I worry that I’m too old for the women at the university. They are all in their very early 20s, and as such, I feel like I am inherently determined to be creepy and to have made terrible life decisions simply because I’m older than all the “normal” students. (It’s not even just the women in that aspect, I feel like everyone’s eyes are on me because of it.)

Because of my situation, paying for university, while also paying for a car, working at a retail customer service job (even working full-time hours), I have not been able to afford to move out of my parents’ house. (The school is only about 20 miles away so I commute.) It’s not like I’m the stereotypical lazy moocher living in the basement: I do a lot of work around the house, and I keep my space of the house very clean as well. But because of this, I feel like all the women who have already graduated college will not want anything to do with me either, being past the point of tolerating men who are in college and/or do not have real jobs and homes of their own.

I feel like I’m the only one who’s in this position most of the time, and it leaves me feeling rather isolated. Is there hope for me with any demographic? Or should I not even bother trying until I’ve graduated and found a real job and a place of my own?

Delayed Adult

DEAR DELAYED ADULT: First of all, you’re only five to six years older than the average college student. That’s not an insurmountable – or even terribly unusual – difference in ages. Hell, if you go by the cliched guideline of “half your age + 7”, then you’re firmly within the boundaries of acceptability. When I was in college, there was a wide range of ages – most of my peers were around my age, but there were many, many people in class who ranged from their late 20s to their mid-40s and nobody thought twice about it. Some folks get a later start than others, some get into college late after military service, others were only able to wrangle the finances to go later in life.

The awkwardness you’re feeling? It’s mostly in your head. I say mostly because yes, there will be some judgmental pricks who think that anyone over the age of 25 is ancient and wonder what you’re doing there. That’s all well and good – they’re a—-holes, and you wouldn’t want to date them in the first place. They’re doing you a favor by self-selecting out of your dating pool. Pay them no mind because ultimately they’re irrelevant to your life. Being creepy is about behavior, not life circumstance. If you’re not acting like Humbert Humbert around your younger female classmates and socialize with them like you would anybody else, then you’ll be fine.

Don’t forget: the economy is still in the crapper, housing is scarce and expensive and everyone’s overloaded with debt. There are lots of people who have to live with their parents even after they feel like they shouldn’t. Hell, all things considered, what you’re doing is pretty damn impressive. You’re paying for school AND a car while working full time in a customer service job? All of that is a testament to your ability to prioritize and get sh-t done.

Now I’m not saying that it’s going to be easy, but it’s not the hopeless case you’re picturing. Everything is in how you present it. If you’re going to carry yourself as some hyper-developed man-child who can’t hack it in the real world then of course people are going to not respond well. If you present yourself as somebody in a tough situation who’s doing the hard work and making the sacrifices to get out of it? That’s another thing entirely.

So you live with your parents: big goddamn deal, that’s a temporary necessity so you can pay for your education. You’re working retail – ok, but not only are you paying for school and a car, you’re showing that you’ve got ambition. You’re not coasting through life in some prolonged pseudo-adolescence, you’re busting your ass to make the most out of yourself. That’s something to be admired. If people can’t respect that, then forget them, you’re better off without them.

I do think you’ll find in trying to date amongst your fellow students is trying to find someone you can relate to. When I was in my late 20s, I had a hard time dating anyone younger than 24;  past that, we were simply at such different points in our lives and had different priorities and cultural reference points that it really wasn’t going to work out beyond the very short term. But there will be people who are more mature and who aren’t living the life of the stereotypical college student. Those will be the ones you have the most compatibility with. There will also be plenty of women outside of your classmates; consider meeting up with some of them.

Just remember that other people are going to take their cues from you. If you come across as confident and that it’s no big deal, then they’ll respond the same way.

DEAR DR. NERDLOVE:  I’m a recent fan of your website, I believe the direct approach you normally use is excellent for those of us that drift among decisions.

Speaking of which, I hope to receive a piece of advice from you. I’m a 30 years old single man living in Mexico City. I still live in my parents’ house, I have a steady income and a steady job, but I have plenty of difficulties with the socializing and meeting new people areas, especially women.

 So far I’ve only had one serious relationship (in my college years, 8 years ago approximately, it lasted a couple years) and a few flings, but nothing serious. The thing is, I have recently resumed my friendship with my longtime high school crush, only to discover that I still have feelings for her (or at least that’s what I believe).

 She’s also a 30 year old woman, divorced, with an 8 year old son and a boyfriend/concubine that lives with her at her house. She has financial issues, and she’s also the only income in the house. Her boyfriend is like another child in the household, and of course she’s having problems with her former husband. As I was saying, we have recently resumed contact, we support each other, and I lend her money when she needs it, we talk about life, and I still have feelings for her, I can’t help feeling a strong attraction. Recently we talked about life and love and things like that, and I asked her  if she would consider date me if the circumstances were different, she said yes, but it was not a definite answer, it was more of an ambiguous thing.

 She also said that she will draw the line, and if her boyfriend doesn’t get a job in the next few months, she will kick him out of the house (which not necessarily means the end of the relationship). Also, I should mention I heard this thing before, and nothing ever happens. He doesn’t want to, or can’t get a job, and she doesn’t kick him out.  At the end of the conversation, she offered to introduce me a single friend of her, and that thing caught me off guard.

 I don’t know what to think or do in this point. I’m not so naive to think that she’ll realize everything I’m doing for her and eventually run into my arms, that would be simply stupid.

 The thing is that I feel this situation is overwhelming, I´m 30, single and still living with my parents. Meanwhile all my friends are either getting married or having babies (or both like my best friend’s case) , the peer pressure is terrible.

 I should also mention that I have no problem with her single mom status,  I believe I’m mature enough to handle a relationship with a kid involved. Of course, I wouldn’t mention it to my parents immediately, but I believe I’m mature enough to handle the situation if necessary.

 I would lend a hand financially speaking if necessary, that means no problem to me.

 I don’t know what to do. 

 Either I come clean and tell her how I feel (with the risk that she won’t talk to me or see me again) or I ignore my feelings for her, then move on and accept the blind date with her friend (as an action that will symbolize my defeat with her and my “moving on” attitude).  I don’t want to lose what I have with her right now, but I know that it is simply not enough for me. But then again I prefer a friendship, over not seeing her ever again.

 Help me Dr. NerdLove, you’re my only hope.

Prince Charming To the Rescue

DEAR PRINCE CHARMING TO THE RESCUE: Hoo boy.

Let’s start with the most immediate of questions: the possibility of a relationship with this friend of yours. This is what I would tell you if she wasn’t your long-term crush and just someone you were starting to flirt with and things were going well:

Don’t do it. FOR THE LOVE OF GOD don’t do it. This is a train-wreck waiting to happen. It’s already a complicated situation with her being a single mother and you having virtually no dating experience at all. Dating a single parent isn’t something to be entered into lightly; not only does she have her own life to consider, she has to consider what’s best for her child. She will always have obligations and responsibilities that by necessity will take precedence over you. And should things be even remotely serious – as you’re hoping for – you’re not going to just be involved in her life but in her child’s as well. You are, in effect, going to be having to negotiate two relationships for the price of one; this can be tricky under the best of circumstances, and doubly so when you have very little social experience.

And honestly, your hesitancy to tell your parents that you’re dating a single mother is a pretty good sign that you’re aware that this is likely more than you can handle.

The other reason is that her social life is already a mess. She’s in conflict with her ex-husband – who presumably is always going to be a factor in her life – as well as her shiftless, lazy boyfriend. And, let’s face it, she’s not terribly interested in losing him yet; for whatever reason, she has yet to follow through on her threats to kick his ass to the curb. Maybe she loves him more tan she’s exasperated by him, maybe she’s afraid to be alone, maybe she’s prone to bad decisions, maybe they’re locked into some co-depended cycle that just replays itself over and over again… who knows. Regardless of her reasons, this is one giant, heaving mess of bad decisions that you’re trying to insert yourself.

On that score alone, trying to date this woman is a holy-shit-super-bad idea under the best of circumstances. Now let’s take it up to the next level here with the rest of your situation. You’ve had a crush on her for at least 14 years, even with zero contact between the two of you. This in and of itself is a warning sign: you’ve had an especially nasty case of Oneitis - the belief that she is the one and only special person in the world that you could possibly love. To make things worse, you’re compounding it with White Knight Syndrome, believing that you can earn her love by sweeping in there like a knight in shining armor and taking her away from this life of privation and heartache. Hell, you’re already giving (not lending; you know as well as I do that you’re not going to see that money again) her money on the regular. All of this is a very big sign that you are not equipped to handle this relationship. And let’s face it, you can say that you don’t expect her to notice everything you’re doing for her, but you sure as shit are hoping she will.

Look, just between you, me and everyone who will read this: this is about wish-fulfillment, not about about her as a person.

You’re already somewhat socially isolated. You’ve been feeling the overwhelming pressure to get married and pump out some kids, coupled with your embarrassment at continuing to live with your parents and your generalized anxiety over your difficulties in socializing. Suddenly you high-school crush is back in your life, representing everything you could want: an instant family, the chance to finally achieve an old fantasy and even be the gallant hero, hauling her out of a horrible situation and into a new and glorious life for you! You are more in love with the idea of her and what she represents. I don’t doubt that you’re attracted to her, but she’s much more of an aspirational figure than a real person, and all of those niggling details – her relationship with her ex-husband, her current boyfriend, etc. – are not going to go away. These are all going to be part of her every-day life, even if she liked you back in the first place

But here’s the thing: she’s not into you that way. You’ve already broached the subject of whether she would be interested in dating you if things were different and got a non-committal answer; this is in and of itself an answer. It’s a “no”.  Then on top of that, she immediately offers to set you up with a single friend of hers. These are not the actions of a woman who is considering you as a potential boyfriend or husband; this is someone who likes you as a friend and appreciates your emotional (and financial) support, but simply doesn’t return your feelings and is trying not to hurt you.

I don’t mean to shatter your dreams, but this is simply not going to happen. She’s not going to dump her boyfriend any time soon and, even if she does, she’s not going to fly into your arms.

What you need to do right now is work on yourself some. You’ve got a good base to start with; having a steady job and reliable income is important, especially with the way the economy is right now. Spend some time improving your social skills and meeting people. Check out a couple of my books, read through my site and learn how to improve your dating skills. You should also consider reading Succeed Socially, another site I recommend. If living with your parents is something that’s causing you anxiety, then start saving your money and make plans to get your own place. The more you get your life in order, the less pressure you’re going to feel to rush out and try to play catch-up with all of your friends.

Go on that blind date. The more dating experience you have, the better you will do with your future relationships… and you’ll find that your Oneitis will fade as you start to get to know all the new and amazing women out there.

Good luck.

Dr. Nerdlove is not a real doctor. Please send your questions to Dr. Nerdlove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com)