Ask Dr. Nerdlove by Harris O'Malley

I Ruined My First Time. How Do I Regain My Confidence?

DEAR DR. NERDLOVE: So after having no relationship or sexually experience I recently hit all the check marks (losing weight, positive thinking, social confidence etc…) and things were going great! I met a great girl, attracted her, went out on dates. Then, out of the middle of nowhere one night, she wanted to sleep with me:


Literally straight out of a movie. Quirky entrance into the house where we climbed through a window, wine on the pants followed by “let’s get those off”, followed by “come sleep in the bed with me”. Except unlike in the movies, I wasn’t completely ready, got too in my own head, panicked, and slept on the couch. The attraction fizzled and the relationship never went anywhere.

And ever since I’ve been fumbling EVERYTHING. My confidence slid, I’m not as smooth as I was before, can’t really get a date, and I’ve just been on a rocky road for some months now. Because in my head that night was what it was all leading up to, and if I can’t deliver then, how can I deliver ever? I still feel like deep down any second I’m going to be revealed as a fraud and slip permanently even after working so hard.

How do I get back on track?


Fumbled the Touchdown

DEAR FUMBLED THE TOUCHDOWN: It’s understandable that you’re having self-esteem issues, FtT. There you are, about to have the sort of first time experience that you only expect to see in 80s boner-jams… and you just can’t make it happen. Not only that, but apparently you wiff so hard that the entire relationship fizzles out and now you’re left feeling like all of the experience and good times you had up to that point went with it.

But that’s not it. That’s not it at all. The fact that things didn’t play out exactly the way you hoped or dreamed doesn’t mean that you’re screwed (er… as it were) and you can never manage to achieve anything.

I mean, hell, if we look at this from the lens of raunchy teen-sex comedies… well, this was the 2nd act twist. This was the point of “OH HE’S GONNA MAKE IT!” and then there are misunderstandings, wacky hijinx and now you’re left running out the door with your pants in one hand and your junk in the other. But the whole point of that near miss wasn’t that it sets him back to zero; it’s that it sets him up for the real first time that’s gonna come with the third act and the person who’s actually right for him.

(Unless we’re talking The Last American Virgin, which is almost traumatic in its nihilistic realism at the end… but that’s a different rant entirely).

I don’t think you’re in nearly as bad shape as you think you are, FTT. I think you’re taking things far more seriously than they actually are and the feeling that you “couldn’t deliver” is screwing with you. But the thing is: this isn’t a case of “you couldn’t deliver”, such as it is. It’s that, for some reason, this didn’t feel right to you or you just weren’t ready for it. That’s all. That doesn’t make you less of a man or a failure, it just means that this specific instance wasn’t going to work. And honestly, if you had a little more experience, you probably would’ve been able to snatch victory from the jaws of defeat. In this case — because hindsight is 20/20 — if you’d opted to sleep in bed with your partner at the time instead of running for the couch, you two would’ve woken up in the morning and had the opportunity for another go. You could have said “hey, I seem to be having an issue/a little too much to drink, how about we sleep on it” and then been golden.

But that’s for next time.

What you need to do first is see if you can dig into just why you panicked. Was it a case of deservedness, where you felt like you didn’t deserve to lose your virginity to her? Was it a fear that you wouldn’t have been any good in bed? Perhaps this wasn’t how you wanted to lose your virginity, which is completely valid. The more you can interrogate why you were so in your own head and why this incident threw you for a loop, the more you’ll understand what triggered things. Understand that and you have a two-pronged approach. In the short term, if you know your triggers, you’re in a better position to find ways to avoid them. That way, when the opportunity arises again — and it will arise again — then you’ll be ready and willing and able to avoid stepping on those landmines on the way to the bed. In the long term, understanding the root cause means that you can address that anxiety directly and work towards becoming even more confident and self-assured.

But the thing to keep in mind: this is just a bump in the road FtT, a 2nd act twist to make the audience feel even more invested in the hero’s inevitable success. What happened in the moment was just that: the moment. It’s neither permanent nor an indication that you’re less of a man in any way, shape or form. It may help to take the expectation for sex off the table for a bit. Go out, date and have experiences… but do so just with the intention of going on dates and having experiences. Taking the pressure off yourself to perform can help ease your anxiety and make it easier to just focus on connecting and enjoying your time with your date.

And if things go your way… well, this time, you’ll be much more relaxed, much more confident and ready to have an incredible experience.

Good luck.

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