DEAR DR. NERDLOVE: I’ve been a viewer/reader of your site for a while now, and I’ve even read your book, and I’ve got to say you have a lot of great advice. I’m not historically one for asking advice online, but there’s something I’d really appreciate if you could help me with.

My core problem is this: I still live with my parents, and I’m finding it to be a massive psychological (if not physical) hindrance to getting involved in the world of dating.

To provide a little context, I’m 25 years old (and turning 26 in a couple of months). I graduated from university about a year ago with a music degree in saxophone and composition (very lucrative, I know), and I’ve been living at home and slowly building a clientele of saxophone students since then. I’m making enough money to pay my bills but not enough to move out, and while my family is happy to support me and I love them very much, I’m dying to get my own place and become more independent. For further context, I went to university in the same city my family lives in, so I’ve basically never left home.

While I’m aware that my living situation isn’t terribly unusual for someone my age in today’s economy (my city is on the expensive side too), it still bothers me. When coupled with my rather lackluster dating history, consisting of one brief fling in high school and about a dozen attempts since then that amounted to nothing, my morale when it comes to dating is pretty low. A couple of years ago I had kind of decided that I wouldn’t bother trying to date again until I moved out, but now I’m not sure exactly when it’s going to happen and I don’t know if I really want to hold myself to that. I don’t know if it’s wise to hold myself to it either. I’ve been interested in someone or other at just about any given time in my post-pubescent life, so it’s not that I don’t feel the urge to date.

To be clear, I don’t have any major hangups about my looks or my personality. I think I look decent enough when I care to trim or shave and put some actual effort into my appearance, and I think my personality is good aside from a few minor foibles. It’s mostly just my stereotypically pathetic “mom’s basement” living situation (although I don’t actually live in the basement) and my lack of dating experience and success that’s giving me problems. Telling potential dates that I still live with my parents isn’t something I really want to do, but I figure it has to come out sooner or later. I dread the hypothetical “Want to go back to your place?” that I have to meet with an awkward “Haha, here’s the thing:”.

Anyway, I’m not here to write America’s next seminal novel, so I’ll wrap it up. Basically I have a confidence problem, driven primarily by my living situation and secondarily by my weak dating history. I want to get out on the dating scene, but I’m afraid that nothing significant will or can happen until I’m living out on my own (or with roommates who aren’t relatives). I’d rather not bother at all if I’m doomed to rejection down the road. Am I right to be worried, or is this unnecessary concern? How can I cope with this? What should I do?

Sincerely,

Sax In The Basement

DEAR SAX IN THE BASEMENT: There’s this thing I see people do all the time: they try to game out scenarios in their heads before they actually are in a position to test them out. In theory, this is supposed to be a way of psyching yourself up and getting yourself ready to actually Do The Thing. In practice, this becomes a classic example of worst-case thinking, a cascading series of What-Ifs that inevitably plays out in the most humiliating way possible. What’s supposed to be an exercise in planning and confidence building ends up becoming a case of letting your brain weasels out to play. So even though you theoretically have total control over the scenario in your head, your anxieties take over and suddenly you can only imagine things playing out in the worst way possible.

And because our brains such at distinguishing what we imagine from what we actually experience, we experience the anxiety and fear of that rejection over and over again. We’ve gotten so used to it that we can’t actually imagine things playing out any differently.

And so… you’ve basically set yourself up for failure. Like the s

ttiest version of the Midnighter, you’ve played that interaction in your head a thousand times and you know how you’re going to get shot down in flames every single time.

And that’s the problem, SitB. You don’t have a living situation problem and you don’t have a confidence problem, you have a fear problem. Your biggest dilemma isn’t that you’ve been rejected for living with your parents, it’s that you expect to get rejected for living with your parents. You haven’t struck out yet because you haven’t even stepped up to the plate in the first place.

Your living with your folks? Your lack of dating experience? Those are just excuses. You’re afraid of the getting rejected. The reasons are just flavoring to the stew of anxiety you’re serving yourself.

And hey, guess what? You’re going to get rejected because everybody does. Nobody out there, not Michael B. Jordan, not Brad Pitt, not Chris Evans, goes 5 for 5. Everybody gets turned down and turned away because hey, not everyone’s gonna like you! So yeah: some women will turn you down for living with your parents… just like some women will turn you down because you’re a saxophone player, or because your hair is the wrong color or because you look like their ex or because sun is aligned in Sagittarius.

It’s like playing blackjack: you can do things correctly and build the odds in your favor as much as possible, but there’s always going to be factors outside of your control. You can’t make yourself rejection-proof because at the end of the day, a lot of rejection has nothing to do with you and everything to do with the person rejecting you.

As much as it sucks, rejection is part of the game and there is no avoiding it. Much like studying martial arts or playing contact sports, if you’re actually going to do more than just observe from the sidelines, you have to accept that eventually you’re going to get hit. The key is learning how to take the hit and – more importantly – realizing that you can take it. And to be perfectly honest: you’re better off taking the hit early on and learning how to shake it off than you are to keep letting it be this huge thing that just gets scarier and scarier. The longer you wait for a time when you won’t get hit (which doesn’t exist), the bigger it will loom in your mind and the worse it will be.

Now having scared the piss out of you, let me reassure you: it’s not nearly as bad as you think it’s going to be. The fact that you live with your folks, for example, isn’t the dealbreaker you think it is.  In this day and age, more and more people your age are living with their folks – more than a third of millennials at this point. The economy sucks for average folks, housing is expensive as s

t in most major cities and everybody’s overloaded with student debt. Most of the people you’re likely to meet and want to date are going to recognize that this is a reality of the modern economy, not a failure to launch.

And to be perfectly blunt, the bigger issues you’re going to face living with your parents are going to be the same you’d face living with roommates: namely “bringing someone back home without announcing it to everyone in the house”.

Now here’s how you deal with that fear of rejection: you accept that rejection happens, that it sucks and all that it means is that you and that person weren’t right for one another. You don’t invest emotionally in someone you’ve just met – especially someone who has no empathy for your living situation.

Similarly, you don’t treat the fact that you live with your parents as this huge, shameful secret. It doesn’t define you, it doesn’t mark you as a loser. It’s just part of where you are now. All you need to say is “Yeah, I’m living with my parents at the moment. Trying to find an affordable place in this city is insane” and most people will nod in sage agreement.

Women aren’t as concerned about the fact that you live with your parents so much as “do you have ambition? Are you working to something bigger, or are you just coasting?” You’ve got a job, you’re paying your bills, you’re making moves. Those are all net positives. The rest is just temporary.

So here’s what you do, SitB. Start making progress towards moving out. Save up some money, start talking with friends you could conceivably live with, look at “roommate wanted” ads on Craigslist. It’s not critical to your dating future, but the fact that you’re actually making some forward motion will help ease the brain weasels and give you more confidence. When those brain weasels start to thrash around, you’ll be able to point to those and say “shut up, we’re almost there.”

Meanwhile, stop waiting for s

t to be perfect before you start dating. If you want to date, then start putting yourself out there. You’re worried about your lack of dating experience? Fine: then you go start getting some experience. Go ahead and tell yourself that it’s not for anything serious; you’re doing this just to know that you can do it. Treat it as the casual exercise that it is. If you find someone amazing, awesome. If not, that’s cool too; you’re grinding out your XP and leveling up so that you’ll be even more ready when you do have your own place.

Also: get an app like Hotel Tonight; that’ll help for the times when you need a place to go with your new sweetie and you can’t bring ’em back home.

You’ve got this, SitB.

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 been lacking courage with women in my life, and been taking steps recently to have more courage and take action to go talk to women I’m interested in. Yesterday, I took one of these steps. I went to talk to a performer of the improv show I went to, she was absolutely brilliant (and pretty!). I interrupted her with her friends after the show to congratulate her, and we had a nice little chat, she made conversation with me and seemed interested. She asked if I’d be coming back to the next show, which is in one month, to which I replied I definitely would. Now I didn’t want to bother her as her friends were interrupting, and it was another (scary!) step to take her number right away/suggest we meet again, which I didn’t do. So I wished her good night. (Aside: It’s hard to reconcile being proud of taking little steps while still being disappointed in oneself for not being perfect)

Now the next show is in one month and I think it’s a long time to wait. And I’m pretty good at finding people on Facebook, if you catch my drift.

My dilemma is this: should I contact her online, offering we meet again, or should I wait a month to (possibly) talk to her again? On one hand, I want to strike the iron while it’s hot and act with urgency but I don’t want to make her feel stalked; and on the other, I prefer the engagement of face-to-face but a lot of things can happen and pass in one month, and the logistics of talking to her again could be difficult.

Thanks Doc, keep on keepin’ on

Taking Little Steps

DEAR TAKING LITTLE STEPS: First of all TLC, you should be proud of yourself. You’ve done something that you’ve had a hard time with in the past – going up and starting conversations with people. That’s awesome. Don’t let the fact that you didn’t do or accomplish everything you’d hoped for get you down; self-improvement is a marathon, not a sprint. Take each milestone as it comes instead of getting upset that you haven’t hit the next one already. Trust me: success breeds success, and those little steps add up over time. Take pride in what you have done and let that motivate you for the next step.

So with that in mind, I want to make sure that you don’t screw up your progress and set yourself back by making a couple common mistakes.

Because believe me, tracking this person down on Facebook would be a mistake right now.

Here’s a quick rundown of social media etiquette: certain platforms have different expectations of intimacy. Twitter, for example is an open platform; it’s generally expected that you’re tweeting out to the general public. In an awkward metaphor, it’s somewhere between standing on a soapbox and having a conversation with people out on the street. Some people prefer private accounts and only interact with mutual or approved followers, but for the most part there’s a low expectation of privacy and intimacy.

(Of course, this can quickly lead to problems with people sea-lioning…)

Instagram is similar; it’s an outward facing system designed for people to promote themselves and build an audience of people who want to see their content. While there ARE folks who prefer to keep their IG private and locked to friends only, it’s generally safe to assume that people on Instagram are cool with their content being put out there for public consumption.

Because a lot of people – especially creative types and performers – use Twitter, Instagram and Snapchat for public promotion, it’s not terribly unusual to follow people you don’t know well or know at all.

Facebook, on the other hand, is more intimate. While there are people who will leave their Facebook accounts wide open and who collect as many friends as possible, most people reserve Facebook connections to people who they have a certain level of familiarity with. The accepted level of familiarity may vary – some people will accept friend requests from friends of friends or people they interact with in Facebook groups and professional pages, while others will only accept requests from family and people they know very well. When you get a friend request from someone you only barely know or have only met once… well that can be a little awkward, especially if you don’t otherwise have any social contact with her.

In your case, TLS, you really don’t have a social connection with this person. Unless you’ve left some details out of your letter, you don’t share overlapping social circles or mutual friends to vouch for you; if you did, you wouldn’t have to track her down on Facebook. All you’ve had at this point is one conversation after a performance. And while it’s great that it went well, you’re still a stranger to her. And believe me, having someone who you have met once or twice in passing track you down on Facebook is seriously creepy.

Here’s the other mistake you’re making – you’re overestimating her potential interest in you. As with most things in life, context counts. In your case, you’re coming up to a performer after their performance and chatting with them briefly. They’re still in performance mode, as it were – enjoying the endorphin rush of another successful show, appreciating the kind words and compliments from the audience, engaging with fans, etc. Unless she was going out of her way to engage you, then odds are good that this was her-as-performer; asking if you were going to come to the next show is more about getting people to come back and fill the seats. It’s like meeting creators at conventions: they’re there with a purpose, and that purpose isn’t about making new friends. It’s rare that you’re going to become fast friends after a brief conversation at their table.

So to be perfectly blunt: there really isn’t any urgency here because there’s no emotional momentum to lose.

I know this is feeling kind of harsh and upsetting; despite all appearances I REALLY don’t like stomping on people’s hopes. But right now, you’ve made such great progress that I’m trying to keep you from ruining it by overstepping things and feeling even worse when things don’t work out the way you’d hoped. Believe me, that painful mix of feeling rejected and “how could I be so stupid” hurts way more than dialing your expectations back. Trust me: I’ve been there and done that so many times I bought the factory that makes the shirts.

So here’s what I suggest: hang tight, practice your approaches – both cold and warm approaches – and get better at starting conversations with people. Take the month to just work on being social. When the next performance comes around, see if you can talk to her a little more afterwards. Don’t go into it hoping to get her number; just work on getting comfortable talking to someone you’re attracted to. And if things are going really well, then ask if you can friend her on Facebook. Simply say “hey, I’m really enjoying talking to you, and I’d like to continue later on. Is it OK if I friend you on Facebook?”

If she’s cool with it, she’ll tell you how to find her. If she’s not – she may say she only talks to close friends or family – then… well, it’s going to be disappointing, but you should still be proud of yourself. You’ll have made another significant step. And those steps are going to lead you to some amazing times in the future.

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: This one is going into the “what the hell is going on with my ex” category. You see, we broke up about seven months ago. I was devastated for a while, but managed to heal, more or less (you helped a lot with that, in fact; thanks!). I am currently going out casually with some girls on a “let’s see where this goes” kind of way, but recently figured I might as well try reconnecting with my ex, just to see if we can remain friends.

Problem is: after some texting, she called me and spent hours talking to me on the phone. The conversation got really weird, in fact: she started asking me about my sexual exploits post-breakup, and telling me about hers, in richness of detail. I felt a bit uncomfortable, but hey, no big deal. Thing is, I took that as a possible sign that she was down for some casual sex and started subtly flirting with her. We decided to meet in the near future halfway through the conversation, but she picked up on my hints and said she wasn’t interested. We talked A LOT, and, as a result, she seemed to have changed her mind slightly; she said we should just go out, just the two of us, to see what would happen. She was really busy, and so was I, so we decided to try and find a good day for both.

Three days later, she suddenly messaged me, telling me she was going to skip her night classes for that day, and asking me if I was free. Turns out I was.

That was when things got weird. We started talking about our past relationship, and she mentioned how much of a wonderful boyfriend I was when we were together when the subject “why we broke up” came up. She even said she was sorry if she ever made me feel like I had done something wrong; the problem, she said, was that she felt that was not the sort of relationship she wanted at the time.

The night went on, and I was reminded of how much we had in common, Doc. We discussed philosophy, politics, books; she is a brilliant woman, which was the reason I became infatuated with her in the first place. It is rather sad to say this, but I was reminded of how much she fulfilled me intellectually, something no girl has done for me since. 

To make matters worse, things started getting infused with a weird dynamic. She started pouring her heart out to me, telling me about her deepest problems, about how directionless she’s been feeling lately. Shortly afterwards, she told me about her previous lovers, and about the various levels of frustration she had experienced with them. Regarding this topic, she even seemed to be losing her grip on her own trail of thought; telling me about her fantasies of having a threesome with a guy she’d been seeing, for instance, and about how their fling was cut short when he had to move. She said they “were totally gonna do it” when they met again, only to mention they had a fight via phone months before and that they had become really distant as a result. I asked her about that contradiction, and she told me to not mind her, since she was prone to fantasizing about stuff out loud. Shortly afterwards, we started discussing our own sex life, down to the fact that she often wore low-cut blouses to get me horny, since she knows I love boobs. There was even talk about whether or not what we were having was a date… her answer was, “It could be”.

The entire night was weird like that, down to the touching: sometimes she would encourage me to place my hand on her hip while we walked, sometimes she would gently remove it. Nevertheless, I decided to take a risk and make a move; it didn’t help that she had gone to our “date” with really sexy clothes (a low-cut blouse and a really short skirt – yeah…). I figured, well, why not? Signs are all over the place, she herself put a possible hook-up on the table. I went for it.

She said no. That bummed me out more than it should have, but okay. But, once again, she made me confused with her explanation. She reminded me of how she initially said she was not interested, and explained that a casual hook-up with me would never be just like a casual hook-up with anyone else; since we used to be in a relationship, there are a lot of pent-up emotions between us… which is why we should be careful if we are to get involved sexually again, especially given how emotionally frail she is now (“we both still have the traits that made us fall in love with each other”, she said). The fact that we were still discussing our old relationship, down to the breakup, didn’t help. I half-jokingly, half-seriously mentioned that I should not have made a move, since things would now get weird between us, but she replied that nothing would get weird, and that, if I ever wanted to go out with her again, all I had to do was call her; she would happily accompany me. She even went as far as to say that the fact that we did not hook up this one time did not mean she would never want to kiss or have sex with me again.

And that was it. I drove her home, and for the past few days we’ve been talking semi-regularly. I know how stupid this all sounds; I only realize now what I was getting into. The worst part comes now; I am starting to have doubts, Doc. Throughout the night I thought I only wanted sex, but I am starting to feel like I am developing feelings for her again… and the door she left open, at the end, is only making me feel anxious. She is a direct woman; if she truly does not want something, she does not mince words… or, at least, that is how she has always been. I don’t know how to interpret her actions; is she just keeping me around because she trusts me and sees me as a friend she can confide in? Is she interested in sex, but does not want to rush things because she does not want to be hurt? Or is there something else here? She trusts me enough to pour her heart out to me, that much is true, but everything else is shrouded in fog.

I’ve read your advice on how getting back together with an ex is often just a fantasy, Doc, but let me me honest; I’ve been obsessing over this whole situation. I am still going out with other people, but every now and then my mind darts back to that night. I need a bit of the chair leg of truth, here; how do you think I should proceed? The fact that she is being so difficult to interpret, so emotionally frail, and my own doubts probably mean trying to get back is too risky, but I don’t want to shut her out of my life. I really want to be at least friends with her, but I am afraid that this uncomfortable situation will manifest itself whenever we see each other, which will only end up hurting me. Should I distance myself from her? Should I sit down with her and sort out the situation in a friendly way, so we can dispel this fog and remain friends? Or should I just kick reason to the curb and keep asking her out (she said she would go, after all) to see where this will go?

Allow me to end this by saying one final thing: I was the dumpee, but when we broke up, we both more or less knew what was coming. We were an interesting case; we resonated in an amazing way in some aspects (sexually, too), but other parts of our personalities were just too different. Maybe this is to blame for the fact that I still feel so weird around her?

Thanks in advance, Doc

Stupid Heart

DEAR STUPID HEART: There’s a lot to dig into here, but a lot comes down to what you’re hoping to get out of this.

What I’m seeing is that your ex is trying to sound out exactly what you think you’re doing. After all, there’s a long and glorious tradition of dudes trying to reconnect with exes in order to get “closure”, because they’re horny and want a hook-up or because they’re really trying to get back together but don’t want to be obvious about it.

That initial conversation was pretty clearly her looking to see what you were looking for. Rehashing the break-up, reassuring you what happened wasn’t a reflection on you, talking about what you’ve been up to romantically… these are all pretty standard part of the “are we going to be friends?” script. After all, trying to be friends with an ex afterwards can be tricky, especially if one or both of you have any lingering issues with the break-up. You may have had a lot of emotional intimacy before, but breaking up means having to step back and reassess just how intimate the two of you are  going to be now. It’s easy to accidentally slip into old patterns when you’re with someone you used to date, especially when those old patterns means sharing everything. Those old levels of openness and intimacy can be tricky at times. Some folks are ok with hearing about their ex’s love-lives. Some aren’t, and hearing about it is uncomfortable or reopens old wounds. Some are cool with the bare bones details (“Yes, I’m seeing someone, it’s pretty good”) and others are cool with sharing every single intimate detail down to size, shape and smell. Talking about her previous lovers and her fantasies can be feeling out just where the two of you are (or will be, should this friendship continue), or it can be a subtle bit of games-playing: “see how popular and in demand I am? You should be jealous.” It can even be a hint that she’s down to clown.

Then she noted that you were angling for a hook up and shut that line down. It’s pretty clear that she’s not interested in having a casual thing with you. I mean, she shut you down twice. That’s a pretty solid answer right there.

But the fact that she doesn’t want to have a casual, NSA relationship with you doesn’t mean that she isn’t necessarily interested in you at all. Look at her behavior. It’s flirty, it’s sexually charged, (come on, she points out that she wears low-cut shirts because she knows they turn you on, while wearing a low-cut shirt)  but she’s also setting boundaries; she’s interested in you, but not as a one-night stand or a fling. In fact, I suspect that the times she’d pull back are when you’d be sliding past “flirty” and into “it’s gonna happen” territory. Be honest: when she’d move your hand from her hip, how much had you let it slide towards your ass?

But honestly, you don’t need to read between the lines much, seeing as she flat out told you what was going on. She wasn’t interested in sport-f

king, but talking to you did remind her of all the good times you had together and that moved her. She wants to see what’s going on with you and if you’re interested in more than just a fling. She’s open to dating you again, but she doesn’t want to be hurt and pumping and dumping her will very clearly hurt her so if all you want is a couple of easy orgasms then she’s not gonna be down. Why is she not being more direct? Because she doesn’t want to be hurt and flat out asking you runs the risk of getting hurt if you said no. But being flirty, giving you signs – and let’s be honest these were not subtle ones; she may as well have been using semaphore – and leaving the door open for you to make the next move gives her enough plausible deniability to let her salvage her ego if you’re not into it.

There really isn’t any uncertainty here, SH. It’s pretty clear what she wants. Now it’s just a question of what you want.

When it comes to getting back together with your ex, there’re generally three questions that need to be answered.

1. Why do you want to get back together?

2. Why did you break up in the first place

3. Have those circumstances changed?

With numbers two and three, the answers are fairly simple: she wasn’t ready for the relationship the two of you have and she seems to be willing to give it a shot now.

So you have to ask yourself why you are starting to get those feelings again. Is it because she represents something safe and familiar, a piece of nostalgia rather than the threatening and uncomfortable uncertainty of dating someone new? Is it because you have unresolved issues with her that you hope to get sorted a second time around? Or is it because your relationship was a case of “right person, wrong time?”

It sounds to me like what you really want is to give this another chance and you’re looking for permission to try.

And frankly, it sounds to me like your ex is hoping you’ll give it a shot.

I say go for it. Take it slow, be gentle and see where it goes. The last thing either of you need is to be hurt again.

Good luck.

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