Did I Get Dumped for Being Bad at Sex?

Dear Doc.

I am 39-year-old male virgin. Thanks to blog similar to yours, but in my language, I started working about my mental hangups and, after almost 20 years, started putting myself out again.

I met woman on dating site and after 2.5 months of talking to each other by communicator (1-5 hours a day, literally about everything, including flirting that edged on phone sex) we met in real life (weekend in rented place about halfway between our towns). Our physical relationship lasted all of 4 hours. We landed in bed less than 2 hours after we met IRL, and after some making out (I kissed a woman for the first time), we ran on a problem. She got into it hot and heavy, maybe faster than I was ready for. I wanted sex on that outing, had condoms, lubricant etc. but thought that we will get into it more organically, you know, cuddling, then kissing, enthusiastic consent and baby steps. As it turned out I misread the situation and my attempts at asking for consent or guidance were buzzkills.

We started three times into heavy petting zone, and every time when I asked about how to do it pleasurably for her, she lost the mood. After the third time, she told me that next time I need scenario in my mind, and that sometimes lack of ‘no’ means ‘yes’. After that she left and gone straight into train home. I talked with her after that (after using rest of that weekend for recovery) and she tried to be supportive, but it included suggesting finding myself partner which have as much lack of experience as I (she suggested disabled and people with mental problems and I think she really saw it as being helpful).

After that I am plagued with a question if we were simply not matched sexually or am I that bad in bedroom because of my lack of experience, that I need to patronize sex-worker to lose my V card and get remedial education in treating woman in bed before risking ruining another relationship?

Best regards,

Maybe I’m Not Ready For Sex

This is easy, MINRFS: this was a her problem, not a you problem. Yes, there were some things you could have done differently, and we’ll cover those, but those weren’t necessarily deal breakers and wouldn’t have been with the right person. Instead, this entire experience has absolutely nothing to do with your being a virgin and everything to do with her not being someone who was right for you.

Let me start off with something very important: you were 100% right to ask for consent and to check in with her. Asking if she were cool with things and wanting to make sure she wanted to keep going is a good thing. I will be honest: her saying “sometimes a lack of ‘no’ means ‘yes’” is enough to put my hackles up. While I’m sure she doesn’t mind someone just assuming or taking a lack of a “no” as permission, that’s not going to be true for everyone and treating it as a universal rule is a great way to set someone else up for failure. Even if we assumed that women were evenly split and it was a literal coin toss between “please ask” and “asking turns me off and I will end the date”, it’s better to err on the side of seeking enthusiastic consentsimply because the consequences of being wrong are much higherfor everyone involved.

If you ask someone who finds being asked kills their arousal, then all that’s happened is that your date ends early and in an unsatisfying manner. Sure, that’s disappointing, but disappointment is a very small consequence to face when you’re trying to make sure that your date wanted the same things that you do. On the other hand, if you don’t ask and the other person didn’t want to go further, now you’re potentially causing actual harm. Asking, even if asking would be a turn-off, is still the better choice.

(Also: it doesn’t take much to make asking into something incredibly sexy. If someone’s really into you, it’s very hard to ruin the moment, and asking for consent isn’t going to hit that bar. However, by folding asking for consent into part of the seduction, you turn a simple question into something that can be very, very hot.)

What she says later, however, makes me think you that you dodged a bullet by not having sex with someone who sounds like a horrible human being. Telling you to find a partner who’s disabled or has a mental handicap because they’re more “your speed” is the sort of thing that makes me say “My dear sister in Christ, run that shit by me again…” because my first thought would be “you can’t possibly have said what I think you said” and my second thought would be “what the actual pluperfect thundering FUCK is wrong with you??”

So, while I’m sorry you missed your chance to lose your virginity, and I empathize with how frustrating this was… my guy, you honestly lucked out because this was not someone you wanted to have sex with.

So what could you do differently? Well, to start with, I think it would’ve been good to talk about what you expected and what you might want or need, before you got together. It sounds to me like the expectation for both of you was that you were meeting up specifically to have sex. Even if that hadn’t been said explicitly and openly, the increasing flirting and near-phone-sex made it clear that sex was a strong possibility. In general, I’m a fan of what’s sometimes called the “Safe Sex Elevator Talk” – what you like, what you need, what your turn-ons are, what your turn-offs are, what you absolutely won’t do – basically giving them the “here’s what you need to know in order to win with me” guide.

The benefit to this is that it lays out information that a good sex partner would want to have. After all, someone who’s worth having sex with is going to want to ensure that you have a good time, just as much as they do. And in this case, I think saying “here’s how I’d like things to go” is entirely appropriate, especially since this would be your first time.

In point of fact, I think telling her that you’re a virgin and might need a little guidance would be a good idea. I don’t know if you told her you were a virgin before you met up, or whether it came up at all, but it’s information that would be worth her having. If she were someone who absolutely didn’t want to sleep with a virgin, it would give her an opportunity to say “ok, I don’t think that’s something I’m up for”, before you spent money on the hotel room or the Airbnb. But if she were someone who was interested in being your first, it might well change how that first night proceeded – especially if she were someone worth losing your virginity to.

Here’s the thing: while I don’t think someone’s first time “needs” to be special, I do think it should be worth it and with someone who’s likewise worth it. In an ideal world, you want someone who’s going to be caring and considerate, who’s going to be invested in your having a good experience overall. To be sure, this doesn’t mean that it isn’t going to be good for her – lots of people have had mind-blowing sex with a first-timer – but it would mean that things would likely have flowed more like what you hoped for.

(And, incidentally, saying “here’s how I’d like this to proceed” is absolutely something you can say. Don’t be afraid to speak up if there’s something you need or if something feels wrong or isn’t working for you.)

I think that her knowing that you were a virgin would also have changed her attitude towards your asking for a little guidance or encouragement. To be fair: sometimes the way a person asks can be a problem. But at the same time, context also matters, and the context of “I have literally never done this before” makes a difference.

Part of being a good lover is paying attention to your partner’s behavior and learning to read their reactions and responses – this gasp means “yes please keep doing that”, that gasp means “ow, I didn’t like that”, her grabbing your head and pulling it in tighter means “if you stop what you’re doing, I will absolutely murder you right now and no jury will convict me” and so on – and saying “do you like that” or “how does this feel?” can be part of it. But it can be irritating or a bit of a buzzkill if someone is constantly asking ‘is this good’, or ‘how should I do this’, like someone asking every couple minutes for help or instruction with a simple task, especially if they presumably know what they’re doing.

But as I said: you’re a virgin and this would be your first time, ever. If she knew that you were a virgin and was down to be your first, one would hope that part of showing you the ropes would be saying “do this” or “you know what I really like? When someone does this…” or otherwise giving encouragement and direction. So, while I can see how you might – and I stress might – have contributed to the buzzkill, I think the real buzzkill was her being a horrible person.

(Seriously, I’m not getting over the ableist shit she suggested any time soon. Handicapped people and people with mental disabilities are people, not fucktoys someone uses for practice what the shit??!?)

Now as I said: I think this was a bad match for you in general and as someone to have your first time with. Would it be worth your time to see a sex worker for your first time? Well, let me ask you this: how do you think you would you feel, afterwards? Would you feel like you got an experience that you wanted, or would you feel like you “cheated” somehow or that this was ultimately a degrading experience or that it said something bad about you?

As a general rule, I’m pro sex-work and pro sex-worker, and I don’t think there’s anything wrong with your first time being with one (with the full that this is someone who’s doing sex work because they chose to and aren’t being coerced or trafficked, etc.). If anything, there’re some definite benefits: you’re guaranteed that the entire occasion is going to be focused on you, your pleasure and having a positive overall experience. But a lot of people have mixed or complicated or even negative feelings about paying for sex in general and for one’s first time in particular. If you’d rather not go that route because you know (or worry) that it’d make you feel awkward or bad, then it’s not for you and that’s perfectly fine.

So, moving forward, I recommend getting comfortable talking and being up front about what you’d like and how you see things going, especially if it’s going to be your first time. Keep in mind: this is intended as a dialogue, where your prospective partner also shares how she would like things to proceed. As you get more experience under your belt and especially if you’re dating someone or getting to know them, you’ll be better able to read that particular person and know “ok, yes, she’s down to do X” or “She’ll like it if I do Y”, but that’s something that comes with time and familiarity.

And more than anything else, let this be a lesson: just because someone is hot and horny doesn’t mean that they’re going to be someone you want to fuck. Make sure that someone you’re going to sleep with is someone who’s actually worth your time and that you’re both invested in everyone having the kind of sex they want to have.

Good luck.

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Dear Mr. Doctor: long time reader, first time caller, all that jazz. I’ve seen you talk about making small talk and asking questions and all that but what do you do if the other person just won’t respond half the time?

Let me explain.

I made a resolution this year to be closer with my friends and strengthen our friendships, because I feel like most of my friendships are actually pretty shallow and I’d like to change that. Among the people I’m trying to be closer with is a female friend of mine, about 6 or so years younger than me. She originally ended up in my social circle because she was the cousin of one friend and dating another, but stayed around after they broke up, because we all thought she was cool. We’re occasionally flirty but nothing serious and while I wouldn’t mind if something happened between us, I’m not going to go out of my way to try to make it happen. It either will or it won’t and that’s fine with me either way, I’m just trying to have tighter friends, especially since I’m fairly certain she’s casually dating someone. I mention the flirting because I wonder if it’s relevant or not, as you’ll see in a moment.

Recently, I asked if she wanted to grab dinner at a new place in town I wanted to check out and just generally hang out. She said sure, we meet up, get a table, order drinks and half the conversation is great and half the conversation is me asking questions and getting either short answers or awkward silence. 

 I noticed is that if we try to talk about anything personal beyond the very shallow “so, how’s it going?”, she clams up. And to be clear, I don’t mean like I’m flirting when I try to learn more or get personal, I just mean anything that goes beyond whatever happened this week. But if I bring up something like JRPGS or computer games we’re both playing, like Metaphor: ReFantazio or Baldur’s Gate 3 or some other non-personal topic, then suddenly the conversation is easy and starts flowing like a river. Her face lights up, we talk about the characters we rolled, crazy outcomes to things we tried in game, all of that. It’s all easy and we’re off to the races. But then I try to bring it back to some of the deeper ‘getting to know you better’ questions and it’s like a gate comes down, the river is dammed up and we’re back to weird awkward silences again. And I should mention that she doesn’t ask many questions back. 

My personal theory is that maybe she’s worried that I’ve got the wrong idea that this was a date? Except I would’ve said that it was a date when I asked and our occasional flirting aside, I’ve never made anything that I would think could be seen as a move.

I have no idea if I’m doing something wrong, if she doesn’t want to be friends or if there’s some secret third thing I am completely missing. 

So doctor doctor give me the news. What’s going on here and what do I do about it?

But How About Patch 8?

This is one of those times where I think you have to accept someone as they are, BHAP8 and just roll with it.

Now, I wish you had provided examples of what you mean by “personal” questions, because that is a pretty wide range, even with the “shallow” filter. That could cover anything from “what’s been going on at work” to “anyway, how is your sex life?”, and how deep or personal you’re getting could provide some insight to the issue.

Without that level of info, we’re going to have to speculate, instead.

There’re a few possibilities here. One possibility is that yes, you’re right: she feels like you’re trying to go from occasional flirting buddies to something more, and rather than trying to turn you down directly, she’s hoping you’ll get the hint without her having to say it out loud.

I know you never said anything about it being a date, but there’re a lot of guys who’ll try to pull the Schrodinger’s Date card, where you’re both on a date and not on a date at the same time. If she’s worried that you’re trying to rope her into something or that it might be something that could be interpreted as being into you, getting quiet and not playing along is one way of avoiding the issue. This is especially true if she’s someone who’s conflict averse, or really worried about having to directly say “no” and upsetting you.

Another possibility is that she’s the sort of person who feels uncomfortable talking about herself, or may feel like you two aren’t close enough to really share those sides of her life.

A third possibility is that she doesn’t know what to say. I’m sure you’ve had moments where someone asked you something and then suddenly you realized you didn’t know how to answer it. One of the classic examples is “what do you do for fun?” or “what do you like to do when you’re not at work?” and you’re suddenly wondering if you’ve ever had fun in your entire life because you can’t think of a single thing. No hobbies, no outside interests, the inside of your head is nothing but a dial tone as you try to think of an answer and just draw blank after blank after blank. Sometimes being put on the spot like that can just cause your brain to bluescreen and you’re stuck trying to think of literally anything you’ve ever done ever.

A variation on this could be that she thinks her answers to those questions would be boring or stupid or she’s been made fun of for them before, and so she’s reluctant to bring them up. A lot of people – women especially – get told that they talk too much or that people don’t want to hear about something that they get excited for, and so they end up just quietly self-censoring around those topics.

Now, I think one thing that’s significant is that she opens up when you talk about RPGs and video games. Those seem to be things she really loves and gets a lot of joy out of, so they’re things she’s excited to talk about. This makes me wonder if maybe she’s somewhere on the neurodivergent spectrum and RPGs or games are among her special interests, whereas the personal stuff just seems less interesting or less easy to talk about.

The not asking questions part also makes me wonder if she’s the sort of person who thinks “well, if you had something you wanted me to know, you’d tell me…” and asking questions (or asking questions back) isn’t something that comes naturally or effortlessly to her. There’re some folks – especially among my neurospicy bretheren, sisteren and theytheren – who have to consciously remember that asking questions is A Thing and have to make a point of asking questions, rather than monologuing or going off like a rocket when you bring up something they’re really into.

So what do you do about it? Well, you can try a few conversational gambits, like dropping some obvious open loops or unanswered questions into the stories you tell or information you share – things that would prompt more questions from someone who’s trying to engage with you. You could even call it out directly and ask if she’s uncomfortable when you ask about more personal topics. Or say “is there anything you want to ask me?”

But if I’m being honest, I think this is one of those times where drawing attention to the awkward is only going to make her feel more awkward. I suspect in this case that the better move is to let the more personal or deeper questions go for a bit; I think it’s likely that either she doesn’t feel comfortable answering those questions in general or sharing more personal information with you. Since it doesn’t seem like you two have hung out much on your own, it may be that you just haven’t – in Persona or BG3 terms – gotten your social meter with her to the point where she’d feel comfortable talking about herself more. Giving her more time to feel comfortable and focusing on your shared interests – especially since they’re the ones she responds to – will lead to more entertaining conversations for now.

(It’s also possible that she’s just not comfortable talking about herself, period, but my advice would be the same, so it’s a distinction without a difference.)

You might also occasionally drop hints that you’re dating someone else or that you’re not looking at any hangouts with her as a date. Knowing that you’re not trying to pursue something with her might help ease her nerves and encourage her to let her guard down, if that’s the problem.

As it is, having a few ice breakers that don’t feel so personal – did she play the first Baldur’s Gate games and is she more of a Minsc and Boo person or a serious PC character type? Is she more into JRPGs or Western ones, does she like action-RPGs like Skyrim or Oblivion, has she done any tabletop? – could help keep things going. I’d also recommend keeping an eye out for signs that she’s worried that a topic is dull or uninteresting to you; in those cases, make it clear that no, you absolutely want to hear more.

Let her talk about the things she enjoys and she’ll have more fun with the conversation overall. That’ll help her have fun with you in general, which will help strengthen the friendship, even if you two don’t know each other’s deepest secrets. You may get to that point, or you may not, but I think trying to force it is going to have the exact opposite of what you hope.

Good luck.

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This post was previously published on Doctornerdlove.com and is republished on Medium.

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