Fear of Sex, Jealous Boyfriends, and “Am I Just Really Boring?”

by A Dude

I’m afraid of sex! I was a late bloomer. I lost my virginity at 27 and have never had a serious long-term sex partner (I am 30 now). The few times I have allowed myself to have sex (I have a lot of rules) were mostly one-night stands so that in case I was terrible I could just never see the person again. I’ve gotten no complaints but I am still terrified of sex. It is awkward and squishy and weird and I don’t know what to say/do. Usually I’m pretty drunk and the dude has no idea that I A) am going to sleep with him B) have no idea what I’m doing.

Now I’m wanting to date more seriously and stop messing around with random dudes, but before I can be intimate with someone I care about, I feel like I gotta take it suuuper slow. Men my age who are liberal and sexy don’t seem to get that. My real question, therefore, is how do I tell a guy that I’m interested in that I’m embarrassed about my lack of sexual expertise/total awkwardness in the sack? Should I even say anything? I mean, he’ll notice that I’m sexually awkward, right? No one wants to be with a pretty/funny girl who is bad at sex (didn’t you say you’d kill that girl in the marry/boff/kill scenario or something?). I am super pretty and smart and funny and lots of men seem to like me but I am so paranoid about sex that I’m scared of dating. I want this to be the year I get plowed, like, constantly. This is really psyching me out to the point that I didn’t have sex at all this past year : ( Is there still hope for me to have a normal sex life?

Here’s the deal. Sex IS awkward and squishy and weird. It’s pressing our wettest, most secret parts together, in hopes of mutual satisfaction, improved self-regard, and expressing love. But if you’re capable writing the words “plowed constantly,” then you also have an inkling of this truth: sex is awesome.

A very good therapist once told this dude that sexuality is not separate from the other issues in your life. Which is to say, something kept your super pretty, smart, funny self from having sex until you were 27, and keeps you feeling awkward about it three years later. That thing might have to do with sex or might not. Maybe you know what it is and maybe you don’t, but you should talk it out with a professional.

Good news is, while you do your 45 minutes per week, you don’t need to live in a convent. If it’s about to get hot and heavy with a guy you’re interested in, definitely tell him you’re embarrassed about your lack of experience. It may scare him away. But it’s just as likely that he’ll be psyched to educate you and feel relieved that his own hang-ups aren’t under the microscope. He’ll get off on playing the expert and gently showing you the ropes. HOW do you tell him? Sadly, you just gotta say something. The cool thing is, as soon as you mention feeling awkward, you won’t feel so awkward. It’s the same reason couples have great sex after a fight. It’s not really reconciliation. It’s because a fight consists of honest communication, however aggressive, and clear air is full of oxygen that fuels humping.

Sure, people want to get with the pretty, funny girl who’s no good at sex. Once. Dude will proudly tell his friends about how you downed three shots, went home with him, and then lay strangely still while he banged away. Enjoyable enough, hence the lack of complaints. But they weren’t one-night stands because you kept your identity secret (chances are you’re a Facebook search away), but because he didn’t look for you. Dig in with a therapist, get your courage up to mention you’re inexperienced, and you’ll have a text waiting before you get home in the morning.

But nope, there’s no hope for you to have a normal sex life. I don’t think such a thing exists. Some couples do it once a week and that suits them just fine. Others bang twice a day in the work bathroom, then go back to their desks. And there’s a guy in Florida in a committed relationship with a plush Dora the Explorer. You’ll find your normal.

My boyfriend would rather kill himself publicly than talk about his feelings. If I ever do something that annoys him (like talk to my ex, or dress too slutty when going out with my girlfriends) he’ll give me the silent treatment for hours and force me to guess why he’s upset. How can I get him to TALK about what he’s thinking and stop wasting my time with these idiotic guessing games? Got any tips on how to turn it into a joke, because I think that’s the only way he’ll ever tell me what’s on his mind.

Either A) your boyfriend is a giant jealous baby, or B) you actually punish him when he speaks his mind.

If B, stop. When you claim to want to hear what’s pissing him off but in reality jump on him whenever he expresses something, no wonder you have to pry it out.

If A, which is MUCH MORE LIKELY, consider dumping him. That may sound extreme, but seriously, there’s no reason to put up with someone so insecure and immature. Any chance you’re dressing “slutty” to attract attention that you’re not getting from your boyfriend, because he… sort of sucks? And are you talking to your ex because you miss being with someone who’s not a cipher-infant? Then you deserve better. Before you get all worried about breaking your boyfriend’s heart, consider the very real possibility that he’s unhappy with the relationship too. If he can’t open up about small stuff, chances are he doesn’t have the balls to end the relationship even if he wants to. He might just be hoping that you do.

If this isn’t ringing true — if you’re happy with him apart from his being closed off, and you think his jealousy means he really wants to be with you — then let him know you love him but are sick of playing psychic, to the point where you’re seriously debating if this is the right relationship for you.

Here’s a joke for him. Woman walks into a bar. No punch line. Just let him know it’s you, and you’re single. If he’s interested in staying together, that laffer might get him talking.

So lately rather than thinking that maybe I am entirely undatable (less attractive girls have done better!) I’ve considered that maybe I’m going for the wrong target market. Is it possible that I’m aiming either too high or too low (because they seem to fit that category, and especially the lower categories, because I really dig nerds)? Is it possible that I’m not nerdy enough to date nerds, and not cool/attractive enough to date guys interested in the things I’m interested in? IS THIS A THING? AM I JUST REALLY BORING?

You say you dig nerds, but you separate them from the guys “interested in things you’re interested in.” Which means that nerds fascinate and amuse you, but you’re not spending your Saturday LARP’ing or building a Theremin or defending Jar Jar Binks’ damaged reputation. So you’re a tourist slumming it with the nerds, and I bet they enjoy the attention at first but eventually tire of feeling like specimens. No date three for you.

Yes, it’s possible you’re just really boring. 22% of people are, nerds have concluded. But more likely you’re just wrongheadedly thinking of people in strata, when you’re actually looking for an individual. You are a special person in search of a special person! Ask yourself this: are you into the same things as the cool, attractive people (modeling watches and DJing on watercraft, I assume), or are you into them because they do those super cool things? Which is to say, no, I don’t think that’s a thing, simultaneously aiming too high and too low. But it is a thing to be attracted to what people do and not who they are. And nerd or cool guy, it’s a turn-off.

I just kissed someone whose mouth actually tasted like it was made of canned fish. We had just eaten hamburgers and drank martinis — no fish at all. Just thinking about it again is making me nauseous. I had to come home and wash off my face. The kiss was like two seconds long, also. Has anything like this ever happened to you?

Yes, twice. But both times I was kissing a fishmonster. I’m guessing that’s what you were doing. If the dude was not up front about being half fish/half beast, chances are there are other things he’s hiding too, like not being over his ex or having insane credit card debt. Swim away while you still can!

Update: Joking aside, he may suffer from a rare condition known as Trimethylaminuria, also known as Fish Odor Syndrome. I swear I’m not making this up. It’s a metabolic disorder where you can’t break down trimethylamine, a product of digesting several types of food, including meat. Trimethylamine has a strong fishy smell, and builds up in the sweat, urine — and yep, breath — of the sufferer. There’s no known cure, but charcoal supplements are known to help. Get him suckin on a Brita filter!

OK. So, if a girl has been having this casual yet dramatic habit of sleeping with one of your friends, a dude you’re having a bromance with (note: the “you” in this is you, the dude), would it be a big no-no for you to hook up with this girl? Say they have been doing this for two about years and it’s been pretty clear she was at one point crazy in love with him and he… well, not so much. Now she’s started to eye you up, what do you do? (OK, you might not think she’s hot at all or anything but you know…) Or what would you prefer the girl to do? Back the hell off because it’s too damned weird and awkward?

If I’m in a serious bromance with a dude, I respect his taste and am a bit envious of his conquests. Which means I think you’re hot and I would be gratified by your attention. I also recognize that he’s not super into you, and could benefit from some motivation to move on. So in a perfect world you would proposition me, I would get his blessing to bone you, and after we knock Nikes we’ll hopefully fall in love, have kids we don’t traumatize, and retire near a lake.

Here’s the more likely scenario. You and I do it on the sly, he finds out, and gets pissed. Nothing like outside interest in a lady he’s halfheartedly banging to make dude suddenly think you’re territory worth defending. Now he and I are in some kind of fight, and I feel sad. And wait… are you wanting to be hooking up with each of us now and again? That definitely won’t end well. Bromance before homance. So to answer your question, yes, best to back off.

But the real question you should ask yourself is why are you still wasting your time with my friend? My hunch is you’re in your early or mid 20s, in which case this sort of confused foundering is pretty standard, and the resulting drama and sex are entertaining enough while you wait for something more serious. If you’re pushing 30, though, cut it out. Give yourself some space to figure out who you’re really interested in, whether that’s me or not.

I have a close male friend who has never had a real relationship. For some background, I’ve had a serious boyfriend since we met, but since we genuinely enjoy talking to each other (usually about the apocalypse, or Wikileaks, he’s one of those guys), he pursued the friendship anyway. His problem is that he ALWAYS goes for girls who are several galaxies away from his league. There have been plenty of times when cute, cool girls have approached him and shown interest, but he blows them off in favor of pursuing the only girl in the room with whom he has no chance at all.

My friend is a bit overweight, and makes very little effort to take care of himself. So, whatever, he’s fat and hits on chicks who are too hot for him. So what, right? Well, lately he has been doing this exact thing with my roommate and best friend. And not only doing it, but acting like a total fucking creep about it. She’s not interested, but she knows he’s my friend and has been really classy and kind about it. He has misconstrued this kindness as a sign that he should keep trying, and now my roommate and I are both going out of our way to avoid him.

I love my friend — he’s a funny and interesting person with a lot to offer the right girl — but how do I tell him to stop being such a fucking moron, without crushing his self esteem and ruining our friendship? “The girls you think you’re entitled to are never going to be interested, so wake the fuck up” seems a little blunt. This little episode has come after years of him complaining that he never gets past a third date.

You know how the Evil Media tells women that you’d be happy if you were just a little skinnier, perkier, tanner? That same Evil Media tells your buddy that he’s a fuckup unless his girlfriend is the sexiest woman in the room. And it tells him she’s attainable, too. Did he happen to catch Knocked Up or Greenberg or an episode of King of Queens? Common moral: tens secretly love tards. Of course it’s stupid to believe this, but even the most gentlemanly, committal dude occasionally asks himself: why is that lady over there hotter and more magnetic than my girlfriend? Then he remembers, oh right, I love my girlfriend, and perhaps that lady’s boyfriend is jealous that mine isn’t distracted and conceited. Your friend is avoiding this confusion altogether by never getting a girlfriend.

Which leads to the more important point, which is that he doesn’t really want a relationship. It’s fun to flirt. It’s fun to fantasize. And for a lot of people — chicks included, see the 30-year-old almost-virgin above — it’s terrifying to have a real, close relationship with someone imperfect who puts your own imperfections into relief. So he’s good old-fashioned sabotaging himself. Is he still being a douche? Yep, and it’s totally fair to call him out on it. But what he’s doing actually makes sense.

By the way, I’d say it’s your roommate’s job, not yours, to tell him to step off. There’s a point where being classy and kind is just disingenuous, and she’s messing up an important friendship of yours by not giving it to him straight. But it sounds like you’re taking it upon yourself to figure out something to tell him that makes him stop being a creep and helps him out, which is very nice of you. Here’s my advice. Next time he starts whining about the American Apparel model who only went out with his un-showered ass three times, list out the deserving girls whose interest he’s ignored and make him explain why he snubbed each of them. That might be enough for him to get the point. If not, gently suggest that he purposely goes after girls who aren’t interested, not who are out of his league.

Do you know how to give good oral sex?

It’s all about visualizing it right. Dudes just have to understand that it’s exactly like making out, but the whole thing is turned 90 degrees, and you’re REALLY trying to get a Skittle out of the corner of her mouth.

Previously: Nerds, Nipple Hairs, and Blindfolded Threesomes.

A Dude is one of several rotating dudes who know everything. Do you have any questions for A Dude?