DEAR DR. NERDLOVE: Despite all my efforts, my dating life has been awfully devoid of romantic connections, and I have an inkling that I might be creating that problem for myself. Maybe you can help clarify things.

Some background: I’m male and 27. I used to be a shy kid in school, had few (but mostly close) friends. The very idea of opening up to someone romantically was scary and embarrassing. Having blossomed at university, I found what I’d like to think of as my true self. I’m a lot more outgoing and charismatic than back then. Finding friends has become easy and I have a bunch of interesting and social hobbies. And about five years ago, I started dipping my toes in the dating pool and conquering my fear of vulnerability. Huzzah!

Fast forward to now: I’ve gone on first dates with almost 60 women, most of whom I got to know through Tinder and OKCupid. Rarely was there a second date, which I understand is somewhat par for the course online. And exactly twice has there been a connection that was more than “kind of a nice person, but nah”. In both cases, things fizzled out around date three. That, frankly, is frustrating.

One of the conclusions I’ve drawn is that while I think I can play the online dating game fairly well (i.e. find people to go on first dates with), it doesn’t feel fulfilling. The whole experience is just more interesting and intense IRL. That I can work with. But conclusion #2 stumps me: I think have a hard time flirting.

On the one hand, I find it hard to show romantic interest in someone, in particular in groups. “What if everyone sees I might be into her?!” On the other hand, I tend to question my interest. I often wonder how much interest I should have in someone in order to ask her out. What do I need to feel or think about her in order to get physically close? Sure, she’s interesting and I like looking at her – but is that enough to warrant the occasional light touch here and there? I have a hunch that since I don’t overtly/physically flirt in these situations, the women I’m on dates with never get a chance to actually feel if they are, in turn, attracted to me. So it looks like we’re not attracted to each other (or we’re both unsure) but we might hit it off if I just took that leap.

Does that make sense? If so, what can I do apart from making the steadfast resolution to flirt physically (and then chicken out)?

Organic Chemistry

DEAR ORGANIC CHEMISTRY: You nailed it on the first try, OC: you’re not flirting.

One of the things that makes dating more than a little maddening is how often we’re given precisely the WRONG advice.  The UR example of bad advice is “just be yourself”, which sounds reasonable — don’t pretend to be someone you’re not just to be liked — but doesn’t actually help because… well, what about when “being yourself” is exactly the problem?

Just as importantly is the distressing idea that taking an active hand in building a connection with other people is bad or artificial. Men especially are prone to being taught that social fluency — and dating especially — is a binary: either you’re naturally good with women or you aren’t. And if you attempt to learn how to improve your ability to connect with people you’re romantically interested in, then you’re either a loser or a shady manipulator. The idea that people can learn how to flirt, how to build chemistry and forge connections with people is seen as the mark of the conman, the grifter or the pick-up artist and is to be seen with suspicion at best.

It creates a world where we’re supposed to do as little as possible to improve our odds. We passively drift through our lives, expecting fate to do the heavy lifting for us; if it’s “real” or “meant to be” then it’ll happen. If not… well, what can you do?

The problem with this outlook is that it creates scenarios where folks miss out on potentially amazing connections and relationships because they’re stuck in a moment of paralysis; you’re waiting for lightning to strike and generate that chemistry for you instead of taking control of the process and making things happen. It creates these weird moments where we’re lost in our own heads, trying to determine whether or not we should be doing something because what if, what if, what if.

That’s where you’re at currently, OC: you’re stuck in your own head with a bad case of analysis paralysis, trying to figure out whether you should be taking active control or just letting things happen on their own. You need to take a more active hand in your own love life.

The first step towards this is getting out of this mindset that your liking someone or being attracted to them is somehow negative, shameful or puts you at a disadvantage. This “oh no, what if they know I like them” sort of mindset is something you expect in 10 and 11 year olds who’re still working past the “girls/boys are icky” stages or being afraid of being teased for liking the popular girl in high-school. It’s not something that’s helpful or productive in a grown-ass adult. It’s even less helpful when it gets framed as “the one who cares least, wins”.  You need to own your desire and your interest and be willing to communicate it to others. That, after all, is the whole point of flirting: it’s a way of telling someone that you like them in ways that are fun and interesting.

Here’s the thing: one of the things that women hate about dating is the ambiguity and the games. There’re few things more frustrating than trying to read the tea leaves and figure out what it meant when someone did X, Y or Z. Someone who’s fairly straight forward with their attraction and can express it in a clear and charismatic manner? That person’s a goddamn prize. Think of it as clearing away the barriers to connection and helping draw people out of their shell; after all, women on first and second can be just as nervous and unsure as you are. By taking charge and clear the path for them that lets them relax and open up and express themselves enthusiastically, you’re giving them a gift.

The next step is to stop overthinking everything. By trying to gauge your interest — whether you’ve hit the “OK to ask her out” level of attraction — you’re making everything far more complicated than it actually needs to be. It’s much simpler than that: do you find them attractive and interesting? Would you like to know more about them and see if they’ve got more going for them than what’s on the surface? Then ask them out on a date and find out.

Flirting isn’t about meeting some minimum threshold before you can start expressing interest. Flirting is about communication and connection, building interest and attraction through the cultivation of sexual and emotional chemistry. It’s about finding the potential for the two of you, then using that potential as a foundation and building something together.

But none of that can happen until you make it clear that what you’re looking for is a relationship — whether that relationship is for the next thirty years or the next thirty minutes. So if you want someone to know you’re into them, you’re gonna have to show them.

Someone’s gotta make the first move. May as well be you.

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’m a 33-year old man, and I’m writing this because I’ve realized a troubling pattern to my relationships. Namely that, whenever I start one, I become quite worried that she’s far more interested in me than I am in her, and that I’m unintentionally leading her on.

This is vain to an almost grotesque level. I have no reason to think that a woman would be so incredibly into me that her life would fall apart if I expressed disinterest. Nonetheless, I find myself troubled by the irrational fear that she might.

A bit about me: I’m a late bloomer when it comes to dating. I didn’t get my first serious girlfriend until I was 31 years old. In this case, she actually was far more interested in me than I was in her. Due to my inexperience, I didn’t really pick up on this, and I hurt her feelings when I ended the relationship.

This troubled me all through my second relationship, a year later. In this case, my fears turned out to be unreasonable. My second girlfriend liked me, but was not in love with me the way I feared. I will admit to feeling a certain relief when she broke up with me, since it meant I’d never have to worry about this with her.

Now, I’m not saying I shouldn’t keep this concern in mind—I don’t want to become callous. But having this dread hanging over my head is making it harder for me to pursue a relationship. I’m not someone who’d let a bad partner walk over me, but I hate the idea of causing emotional pain to someone who is a good partner, but whom I just don’t love enough.

I have recently met a woman, though we are not officially dating. I’m not sure if she and I will even get to that stage. Nonetheless, I’m have this same fear.

Any advice on how to handle this? 

Too Much To Handle

DEAR TOO MUCH TO HANDLE: First of all, here’s a truth that nobody really likes to acknowledge: in every relationship, there’s going to be an imbalance of feeling. There will always be one partner who cares more or who cares less because hey, we’re human and love is a chaotic emotion. More importantly though is that this isn’t static either; there will be times when one partner is more invested than the other and times when that will switch. As long as those swings aren’t too extreme, it all balances out in the long-run. Welcome to the human experience; none of this shit makes logical sense because emotions could give two shits about logic and fairness.

Second of all: Dude, there’s only one thing to do here: stop overthinking this shit. You can’t control how other people feel, nor are you responsible to manage their feelings for them. You are presumably dating grown-ass adults. This means that they have a responsibility for handling their own affairs – literally. Now, it’s one thing if you’re so afraid of hurting people’s feelings or causing them upset that you’re promising them things that you can’t or won’t deliver on. That’s a shitty thing to do to someone, even if you’re doing it with the best of intentions.

But if someone else is reading more into a relationship than is actually there? You can’t control that. You can maintain a casual frame, sure. You can be clear and straightforward with how you feel about the relationship if they want to have the Defining The Relationship talk. But at the end of the day, people are ultimately responsible for managing their own feels. And frankly, the fact that you’re walking around, constantly on the lookout for signs that maybe, maybe they feel more for you than you’re comfortable with? That’s no bueno, my dude. You’re not only putting up artificial barriers between you and the person that you’re dating – which is going to hurt them more in the long-run than breaking up if the relationship’s run it’s course – but you’re keeping yourself from actually enjoying being in a relationship with someone.

Look, like I said to SitB: rejection sucks. This is true no matter which side of it you’re on. In best dating practices, you want to cause as little unnecessary pain as possible, because pain is inevitable. However, if you’re always going to have your guard up, you’re going to end up making things worse for both of you.

Like SitB, you’re letting these imagined scenarios run away with you and it’s getting in the way of your real life. You need to learn to be in the moment and appreciate what you have now instead of constantly being on guard for those What-If weasels.

Be up front about what you want and what you have to offer. Don’t try to avoid the DTR conversation for fear of leading someone on. But at the same time: just let yourself be present and accept the relationship for what it is, not what you’re afraid it might become. The harder you police other people’s feelings, the more you’re going to end up choking off relationships that might have worked if you hadn’t been so hypervigiliant and guarded.

Don’t let your anxiety close you off from what might be a wonderful experience my dude.

Good luck.

DEAR DR. NERDLOVE: I just found out that my husband is watching porn with Asian girls. I don’t have any problems with him watching porn, I think is pretty normal and understandable. The problem is that now, I’m feeling really insecure. I always knew that he is attracted to Asian women (for the record, I’m not Asian), I know that he has some female friends who are Asian. It’s just that the fact that he is searching for porn with Asians makes me think that he is unhappy not being with an Asian girl. What can I do? What does this mean? Could it mean he’s not attracted to me? Or is this normal?

Worried I’m Not The Right One

DEAR WORRIED I’M NOT THE RIGHT ONE: What does it mean that your husband watches Asian porn? Assuming that he’s not avoiding having sex with you in order to masturbate to porn instead… well, mostly, it means that your husband is turned on by Asian women. But that’s an “in addition to”, not “instead of”.

It’s generally a bad idea to try to divine somebody’s personality or fetishes from their porn habits; it’s rare for someone to be attracted by ONLY one type. Your husband can be hot for Thai or Indonesian, Chinese or Japanese or Korean women and still also be attracted to you. Someone can love large breasts or full-figured women but still love and be attracted to a woman who’s petite. Someone can have a thing tall, Nordic men and still love their Indian boyfriend of average height.

There’re two basic truths when it comes to relationships. The first is that we pretty much all want to sleep with people who aren’t our partners. That has absolutely nothing to do with how attracted we are to our significant others or the strength of our relationships, it’s just part of being human. The second is that no one person can be all things to somebody. For many people, porn is how they fulfill their desires for sexual variety without stepping outside the relationship; it scratches the itch and doesn’t harm anyone.

Now, as I said: if he’s forgoing having sex with you in order to jerk off to his porn collection instead or he’s covertly seeking Asian women on Tinder and his relationships with his female Asian friends is crossing the line from “friend” to “adultery”, then you have a problem. That’s when it’s possible he’s got a fetish that he’s trying to indulge.

(Side note: I don’t advocate snooping to find out if this is true; snooping is pretty much ONLY justified in retrospect. If things are so bad that you’re willing to contemplate violating his privacy, then you might want to consider counseling first.)

But if this is just him indulging a fantasy that doesn’t interfere with the intimacy and affection the two of you have? Then it’s no big deal. Sometimes folks don’t want sex, they just want to skip to the orgasm at the end, and masturbating is the most efficient way of doing that.

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 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)