DEAR DR. NERDLOVE: I’m in my early 20s, female, and at university. I’m short, kinda chubby, and more-than-kind-of a nerd. From a young age, I’ve wanted to be in a romantic relationship. Had a few long-term crushes through middle school, but nothing ever came to fruition. I figured it was just the small school, and that when I got to high school I would have more options and more opportunities. But I had the same issue, only this time I wasn’t single. I ended up dating a guy because I thought that was what you were supposed to do, regardless if you liked him or not. He was horrible but I dated him for seven months, while I had a crush on someone else. The following year, I realized I was bisexual and fell for my best friend. She was kind, but firmly rejected me; we are still best friends to this day. So I graduate, move on to college and I meet a guy I really think could be “the one”. We had an incredible connection with intense flirting and I thought that this was finally going to be the relationship I’ve wanted, but then I find out he’s been pursuing someone else and they end up together.

Since then, dating has been a huge drag. More times than not, I’ll meet someone who’s already infatuated with me for all of the wrong reasons and have to break up with them or I’ll meet someone who I really like and think might be good for me and get turned down. For a while, I thought maybe it was my weight or looks, but I see plenty of girls who look like me in happy, long-term relationships. I’ve asked my friends multiple times to tell me what I’m doing wrong and they always say “nothing, you’re perfect”. I’ve been on-and-off online dating for the past two years, but 99% of people I match with are either lewd, dull, or homophobic. The other 1% never messages back.

A recent development pushed me to write this letter. In order to help him recover from a bad relationship, my good friend of five years and I both redownloaded Tinder. We’re very similar people; both of us have problems with anxiety, depression, and low self-esteem. When we first downloaded the app and started using it, we noticed that I was getting way more people swiping right on me. By the end of the two weeks, I had over 50 matches and he had six. I’ve been on a few dates and nothing has really come of it; the same problems I’ve had before persisted. He went on his first Tinder date ever last night and I’m pretty sure he met his soulmate. At this point, I have nowhere else mentally to turn. If it’s not my appearance and it’s not my mental issues then what is it that makes me so unattractive to the people I’ve liked? I feel like I’ve been making enormous social strides but I don’t even leave these dates with a friend, let alone a partner. Please Doc, tell me what I’m doing wrong.

Sincerely,

Loveless Murphy’s Law

DEAR LOVELESS MURPHY’S LAW: Here’s something advice columnists aren’t supposed to tell you, LML: sometimes there’s not really a lot to be done. We’re supposed to have magic insight and actionable advice, but the fact is that sometimes the issue has nothing to do with you and everything to do with the fact that life sucks sometimes. To quote the sage: you can commit no mistakes and still lose. That’s not weakness. That’s life.

And the truth is that dating often involves a factors that are completely outside of your control. A lot of times, the difference between finding someone incredible and another date to nowhere is just a matter of chance and timing. You may have closed your dating app just as Mr. Right was logging in. You may have met someone awesome, but not at a time when you or they were in a place where they could date. Just as with blackjack, you can influence the odds as much as you can, but chance still controls the outcome.

The key is that you can’t take it personally. It’s hard, I realize. It’s really goddamn difficult to look at all these happy couples and wonder what’s wrong with you. But you’re not seeing what you think you’re seeing. You’re not seeing the whole picture; you’re just seeing a tiny fraction of what they’ve gone through to get where they are – and that’s before we factor in whether they’re actually a happy couple.

It seems like they don’t have to struggle the way that you have because you’re comparing their highlight reel to your unedited footage. It’s all a matter of perspective.  Anybody can look like a massive success if you only see the end-point, not the whole journey.

But their success – real or perceived – doesn’t have anything to do with you. They’re all on their own journey and living entirely different lives. The fact that your friend found a soulmate is good for him, but it has nothing to do with you. For all the similarities you have, he’s living a different story than you. He’s going to have completely different experiences than you because he’s not you.

The key is to remember how much of this is out of your hands and focus on what you can control. You may not be able to force the universe to give you what you want, but you can set yourself up for success. You do what you can in terms of your presentation and putting yourself out there and meeting the right people, and then… you roll with what life gives you.

Some days it won’t come easy. Some days it won’t come hard. And there will be days when it doesn’t come at all. You may need to take breaks to rebuild your strength. That’s fine. Take a break. Love will be waiting for you when you’re ready to give it another try.

It won’t be simple or easy… but nobody ever said that it would be. They just said that it would be worth it.

I’ve seen plenty of people who’ve been in your exact position, LML. They had the exact same problems, the same sense of despair and the fear that they’d be forever alone.

And I’ve been to their weddings.

Hang in there.

All will be well.

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

DEAR DR. NERDLOVE: Reading your articles as an inexperienced man is always reassuring, even when things seem pretty bleak. The truth about me isn’t that I’m socially anxious, terribly ugly (I guess?), or too meek. I’m introverted, but much of my pain is due to not actively trying, and an inferiority complex.

I’ve always been down on myself. I’ve thought of myself as a social reject and someone who’s pretty ugly. I can socialize and make friends, but there’s always been a lack of confidence and low self-worth when it comes to dating. I didn’t have a relationship until I was 26. It tormented me for a very, very long time. I was stressed that my time was running out, bitter that I had wasted my youth. It took me so long to sort out my life and actively try because I was depressed, doing poorly in college, and went through cancer treatment at 22/23. After enduring chemotherapy, I was convinced nothing would ever go right for me. I’m grateful to be in remission, but I’m still a resentful, melancholic and bitter person.

I feel old, like time has passed me by. I wish I hadn’t lost my teens and early 20s, so I feel the pressure to play “catch up.”

At 26, I met a girl who I felt a good connection with. She was going through a hearing (abusive ex), and had also been sexually assaulted. She has had her own issues with depression and anxiety. She would self-harm. I could tell she was deeply in love with me. There was mental connection, but she was also really physically attracted to me. She even introduced me to her parents right off the bat, which was surprising. Our first three months were nice. According to her, I was a good partner, attentive, supportive, intelligent/intellectual, and “made her feel safe.” She had her own insecurities about her body and looks.

I took some time before I started staying nights, because I wanted to respect her boundaries and not push for sex. I made her orgasm pretty easily through oral sex, using my fingers. I was good at foreplay, and a decent kisser. I would make her cum consistently when we were intimate. She would usually initiate, and seemed genuinely into it. I still feel like I fell flat on my face though. This is because I had a few instances of performance anxiety and premature ejaculation. I put such a burden on myself to perform and get a girlfriend that I was super tense. We didn’t ever get a chance to build further physical chemistry and have intercourse. I avoided it, under the assumption that we’d get time to work on things later. I didn’t really enjoy sex, it was more about getting her off. She never ridiculed me, seemed angry or disappointed. She was understanding. Unfortunately, it turned long distance over the summer and fell apart. She broke up with me, saying she didn’t feel enough to keep things going, and she had wanted more closeness.

I feel pathetic that I wasn’t able to perform for a woman who really liked me. I’m not sure I was interested in a LTR, or immensely physically attracted to her. I felt guilty about this. I feared I was “bad in bed” but she had said I wasn’t. I guess I was attuned to her needs. I asked her if she left me because of the anxiety, but she denied that too. She had said that I made her cum faster than her previous partner (the abusive ex). My insecurities are back with a vengeance. I still feel like an inexperienced loser, and certainly still feel like I deserve the label “virgin” (there was penetration but I wasn’t fully erect). I wish I wasn’t so burdened with past insecurities.

I can’t quite feel proud of myself for being a decent boyfriend. I feel like I failed at a fundamental aspect of a relationship. The breakup is not what I’m stressing about Doc. I’m just concerned that I’m an impotent, spineless wimp who squandered the only opportunity I’ve ever had. Kissing three women, and intimacy with one woman doesn’t seem very impressive for a guy who’s now 27. I see many sex columnists ridicule older virgins, but I don’t think there’s anything wrong with me physically.

My question is simple. How do I stop beating myself up? How can I force myself to see that this was a huge step forward for me. It’s in the right direction, at least. I went from thinking I’d never have a partner until my 30s, to having a really loving partner.

Problem is, my sex drive is pretty low, and I’m constantly ruminating on what I did wrong.

I’m more devastated than I probably should be, given the circumstances.

How do I keep going? I feel like this is a sign that I’m not cut out for having a good dating and sex life. I still can’t accept that anyone would actually like me.

-Haunted by the Past

DEAR HAUNTED BY THE PAST: There’s a lot to unpack here HBTP, but I want to lead with this: a lot of your issues are self-inflicted. Don’t get me wrong, I’m not saying that they’re not real or that they’re not legitimate. But a lot of the problems you’re having have less to do with the world around you and the way that you’re looking at it.

I mean, we can start with the way you describe yourself: as a social reject, who’s ugly and has no inherent self-worth. You’ve convinced yourself that nothing could possibly work out for you. And if I can be perfectly blunt… you’re not wrong. Rather: you’re not wrong because you’re going to see everything that way.

See, attitude is destiny, HBTP. The guy who’s convinced that he’s ugly and nobody could love him is correct. Not because he actually is ugly and unbangable but because he can’t conceive of the possibility that someone would find him attractive.

This means that even if someone were to approach him and flirt with him, he’d dismiss the possibility that she was legitimately interested. Oh sure, she was talking to him. She may have even seemed flirty. But clearly she was just being friendly. Or he was misreading things. Or there would be any number of perfectly reasonable explanations for what was going on that had nothing to do with her actually being interested in him.

But the opposite is equally true: the guy who’s confident in himself and his attractiveness is more likely to find women who are interested in him. Not because confidence is inherently sexy – though that certainly doesn’t hurt – but because he’s actually looking for it. He’s more likely to pick up on the signs of her interest because he believes that they’ll be there. And if he’s wrong? Then he’ll chalk it up to being a a learning experience and move on. To him, setbacks, while inconvenient, are temporary. They’re something to be overcome with time and effort.

I mean, let’s look at the example you give, HBTP. Not your ex – more on her in a moment – but on the fact that, holy hopping sheep s

t, you survived cancer. I get that chemo is rough, I’ve had far too many friends who’ve gone through it, but come on! You think thinks can’t go right for you? Sweet Jeebus my dude, you beat the plague of the 21st century! That alone is should be a sign that you have the power to grab life by the hair and start dictating terms. Yeah, being dumped is a shame but God HIMSELF couldn’t put you down.

So much of what’s happening with you is because of how you’re seeing the world. Your ex, for example. You made her almost mythical in her importance. It’s no wonder you were having performance issues; you put so much pressure on yourself that you couldn’t perform. Dicks are divas; there are plenty of times when they’ll refuse to work if things aren’t exactly perfect. Usually at moments when you desperately need them to perform. You put so much pressure on yourself by treating both your virginity and your girlfriend as the end-all, be-all of your existence that I’m less surprised that you had performance issues and more surprised by the fact that your junk didn’t just recoil all the way into your body cavity and call it a day.

And if I’m perfectly honest, HBTP, I’m not terribly surprised that your relationship didn’t last. While I’m sure your ex was a great person, neither of you were really in a place where you could be dating… and she wasn’t going to be a good match for you, regardless. It’s not that you failed at being a boyfriend or that you couldn’t accomplish some critical aspect of being in a relationship, it’s that you were in a relationship that wasn’t going to last, regardless of what you did.

More to the point, however, is that you’re treating it as a definitional experience, when it was nothing of the sort. It wasn’t your defining relationship, it was just a relationship. It wasn’t your forever, but most won’t be. Instead of treating this as a mark of failure on your part, the thing to do is to learn from it for the next time. Because there will be a next time.

There’s nothing wrong with you, HBTP, either as a partner or a lover. While I wouldn’t say you’re a virgin, the truth is, whether you’re a virgin or not doesn’t mean a damn thing. There’s no qualitative difference between someone who’s had penetrative sex and who hasn’t; it just means one has had an experience the other hasn’t. As I’m fond of saying: sex isn’t a test of your worth and women aren’t Mjolnir. Women don’t have “Whomsoever should part these thighs, should they be worthy, will gain the power of Score” embroidered on their underwear.

People have sex for reasons that often have nothing to do with the person they’re having it with. Sometimes they want validation. Other times they’re trying to prove something or get back at someone else. Still other times they’re doing it out of a sense of obligation. And of course, there’re times when they have an itch that they need to be scratched and the other person is the closest acceptable warm body.

The truth is, HBTP: you’re doing amazingly well. You’ve made a lot of progress, got some experience under your belt and – oh yeah – you beat cancer. Your problems are strictly in how you’re seeing yourself and the world… and the good news is that you can change that.

You don’t need to talk to me, you need to be talking with a therapist, my dude. The best thing you can do for yourself right now is to find a counselor to help you work through this lack of self-esteem you’re dealing with. It may take you a couple times to find a counselor and a therapy that works for you. That’s fine. But the sooner you get started, the more you’ll realize that you may not have a lot, but you can turn it into more than it seems.

Don’t let your jerk-brain define you, HBTP. Your experience – or lack thereof – isn’t something to be ashamed of, nor does it mean that you’re deficient or worth less. It’s just a lack of experience; it’s neutral in and of itself. Spend time working on getting yourself in good working order and in a place where you can put yourself out there with more confidence. Your experience will take care of itself. 

You’ve got this.

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 am a female in my late 20’s with a variation of a problem you’ve heard before. I can’t get a date. I never get asked out, and if I ask a guy out they say no. The last guy I dated was in college and we were best friends first and shifted to a relationship as it became clear we both had feelings for one another.

I do plenty of activities where I’m around people. I play D&D with multiple groups of people (forever DM), volunteer at church in areas where I’m around other people my age, go to the gym, play intramural sports, and hang out with friends where I can meet more of their social circles. My friends describe me as fun, friendly, flirty when I want to be, passionate about the things I like, witty, independent, and sarcastic as hell. However, I’m very analytically minded, pragmatic, and not good at showing my emotions. When I jokingly asked which Star Wars character I was most similar to, they all separately said R2-D2 or K2-S0. I am also fairly overweight, but I’m working on it and know that won’t change overnight. I try to look as good as I can, but I stick with minimal makeup and clothes that make me feel comfortable but still look nice.

I have lots of guy friends, so I know I get along well with guys. They take initiative and invite me along to things; it’s not like I’m just tagging along with them. But it’s never more than that. Anytime I try and ask a guy out, which only happens after significant flirting and it seems like they’re interested (and friends tell me it looks like they’re interested-so it’s not just me misreading signals), they say that they only think of me as a good friend. And guys ask out all my single friends, but never me.

What am I doing wrong? I’m not going to mope around and say “woe is me, I’ll be single forever”. If there’s something I should fix, I’ll get right on it. Is it that I’m not attractive enough? Or am I totally missing something else?

Thanks,

Too Many Best Friends

DEAR TOO MANY BEST FRIENDS: Here’s my question for you, TMBF: do you feel attractive? Not in the sense of “here’re all the dudes that think I’m hot,” but the way you think of yourself. Do you look in the mirror and think that you’re sexy? Or do you look at the things that you think are your flaws and think about trying to look good despite them?

The way you describe yourself physically and the way that you describe your appearance makes me suspect it’s the latter. I’ve known a lot of folks, especially people who’re overweight, who look at their weight as the disqualifier from… well, everything. They don’t feel like they have a right to dress well, to put effort into their presentation or to just think of themselves as being a sexy bad-ass. And that sense of “I’m not good enough” tends to get in the way of, well, everything. Because straight talk: there’re folks out there who like big women, just as there’re folks who like big men. And I don’t just mean fetishists or people who think that overweight women are desperate or will put up with more bullshit, folks who are attracted to and desire big women and want relationships with them.

But it’s hard to find them when you don’t feel like you’re allowed to think that you’re a sexy badass.

So my first suggestion for you is to start treating yourself like you’re hot. Find the things that make you feel unstoppably awesome. Maybe it’s a kick-ass dress. Maybe it’s a different make-up routine. Maybe it’s finding your personal style, something that’s uniquely you and makes you feel like a million bucks. This isn’t about changing yourself to someone else’s ideal, but in finding the things that make you feel like a goddamn bundle of awesome that people would be insane to pass up. Because, like I’m often saying, attitude is destiny. And recognizing that you’re money and knowing that people would be lucky to date you changes how you approach relationships and dating.

My second suggestion is to examine how you’re coming across to people. If you’re a little more emotionally reserved and pragmatic just because that’s how you naturally are… cool, you do you. But if you’re holding yourself back because you don’t feel like you’re allowed to have a presence or express yourself… well, that’s when it’s time to give yourself take up a little more emotional space. It could be that your cool demeanor and reserve may be putting people off because they think you’re not interested. It may be that by leaning into your passions and letting those passions be a bigger part of your life, you’ll feel empowered to be more expressive.

My third suggestion is to give things time. Sometimes the issue has nothing to do with you and everything to do with the people around you. It may be that at your age and in your social circles, you’re with people who aren’t mature enough for you; god knows that those guys who like big women often have to overcome a lot of social programming that tells them that their desires are shameful and that they should only want conventionally hot women. It may also be that you just haven’t been in a position to meet the right guy yet. A good friend of mine spent years dealing with assholes who would tell her to her face that she was good enough to fuck, but not good enough to date. She was convinced that she was going to die alone, unloved and unmourned.

A couple years later, I officiated at her wedding.

As unhelpful as it can feel, sometimes the problem isn’t something that you can fix; it’s just a matter of time and demographics and waiting for things to line up correctly. Which ain’t fun… but it also means that this too shall pass.

You’ve got a lot going for you TMBF, and I suspect that the more you embrace your awesome, the more luck you’ll have. Live an awesome life that makes you feel awesome and the rest will start to take care of itself.

Good luck.

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