DEAR DR. NERDLOVE: I’ve been listening and reading your works for a while now, and I have found your insights and advice really helpful —and your obvert feminism and repudiation of pseudoscience wonderfully refreshing, considering what the standards of the industry sometimes seem to be.

I am a 27 year-old straight male that, one year after a friendly break-up that I’ve spent working on self-improvement, feels ready to get back on the dating wagon.

Some weeks ago I met a girl at work whom I found instantly attractive. I got her number and, after another random meeting at work, started messaging her the next two weeks, during a holiday trip she took. What started as simply making sure that my interest was noticed (so that we could maybe meet after her holidays) turned quickly into daily conversations, and soon after into hardcore flirting by both of us.

She proposed to meet the day after she was back, and ended up spending about 10 hours together, from the early afternoon until after midnight. Everything felt natural and clicked, the sexual tension was palpable, and before the date was over we were making out passionately. All in all a wonderful experience.

Thing is: a few days later we met again, and this time she suggested bringing some friends to the meeting. The night was fun and all, but I didn’t feel there was an appropriate time to make out again: no intimate time, no time just the both of us; still, the chemistry was there, so I didn’t make a great deal of it.

Fast forward to a few days ago, when we met alone right before she went again on a trip, and had the conversation I feel really confused and want to ask you about.

She wanted to talk about how she felt about us, and told me that while on the one hand she felt attracted to me and really enjoyed our conversations, and thought we clicked together, on the other she wasn’t sure about wanting to pursue a physical relationship at the moment. She added that there had been times in her life when she felt pressured by the expectations of others to become physical or sexual with other men even when she wasn’t too sure about it, and didn’t want to experience that pressure again. She also said that she was seeing other people, and really didn’t contemplate the possibility of an exclusive relationship for the time being. She enjoyed everything that had happened so far, and didn’t find any fault with me or my doing.

Much of this didn’t bother me: I don’t know that I want anything serious yet, I’m seeing other people too, and, although I’m REALLY attracted to her (sexually and as a person, and I made sure to state this clearly), I’m nowhere close to infatuation.

The question is: should I assume that she’s not really sexually interested in me (her relatively convoluted way of saying that being simply a stylistic choice) and move on? That being the case, how does that make sense after such a (and I really, really don’t think I’m misreading this) passionate and wonderful date, preceded by unmistakable flirtation and followed by what seems to be a genuine interest to see me again and maintain some form of an active relationship (albeit perhaps a non-sexual one)?

The entire story spans only a few weeks, and it ending without getting any further wouldn’t be tragic, but I’m intrigued by what appears to me as an erratic behaviour or inscrutable expectations, and perhaps there is a transcendental truth I’m not seeing to be learnt from this experience.

Not Sure I Understand People

DEAR NOT SURE I UNDERSTAND PEOPLE: I’m gonna help you out here, NSIUP: the transcendental truth to be found here is… literally what she told you. She’s not ready or interested in a physical relationship. More specifically: she’s not ready or interested in pursuing one with you.

A lot of times, after having been on a couple of dates — some times even just one date — people who just aren’t feeling it will do the courteous thing and tell you. And since they don’t want to be harsh or make you feel bad about it, they’ll often add a softener, something that’s meant to take the sting out of it. And since rejection always feels personal — and some dudes really react badly to being rejected — they’ll phrase it in a way that makes it less of a rejection and more of an obstacle that just can’t be overcome. This is why folks will say “it’s not you, it’s me” or  “I’m just not ready to date.” It’s a shame, if circumstances were different then you two would have a chance but they aren’t, so you don’t. Oh well, what can you do, the stars are aligned against us, nothing to be done about it. Occasionally they’ll even add a “right now” to this because, well, it’s not like they’re going to be single forever.

The problem is that while people will do this as a kindness (or occasionally as a way of not getting murked), the people hearing it don’t quite understand what’s actually being said. That’s why when someone says something along the lines of “I’m just not ready to/ interested in/ able to have a relationship”, you have to silently append the unspoken “…with you” to the end of it.  Otherwise you run the risk of giving yourself false hope (or in some cases, ignoring the screamingly obvious) and holding onto the “for now” instead.

Once you start recognizing this, then it’s easier to start working out just what happened.

Let’s look at what happened with you and your friend, NSIUP. You had a lot of chemistry over text, when you met up you had an amazing date that ended with crazy make-outs. All well and good. But the second time you got together, she invited some friends to come too. That in and of itself is… not a warning or red flag, necessarily, but it’s definitely an indication that she wants to ensure that sex or any physical tomfoolery was on the table. That’s something that folks will do when, say, they suspect that their platonic “friend” just invited them on Schrödinger’s Date. So by this point, your friend was sending up a flag of some sort.

The conversation you had afterwards, about how she didn’t want to pursue a physical relationship with you and how sometimes she felt pressured into getting physical when she didn’t want to gives further clarity to her mindset here. This, for example, tells us that the odds are good that her friends were as much chaperones as they were invited to share in cool goings-on.

Now, the interesting part is that she mentions that she’s also seeing other folks. While this could be taken as “so don’t be surprised if you see my relationship status change”, it could also be an indicator of just why she’s telling you this.

So keeping in mind that I’m not a mind reader and the only person who really knows what this all means is her, here’s my best guess at what went down.

You all had a great date… but somewhere along the line she either started feeling weird about things or she started having questions about where this was going. Things may have moved faster than she was necessarily ready for. She may have caught a vibe that you were more into her, and had more expectations, than she was into you. Something you may have said or done may have given her the impression that you wanted more from her than she was ready to (or able to) give. Or that the make-outs on the first date were nice, she wasn’t quite feeling it as much, and wanted to make sure that there wasn’t any awkward “no, we’re not gonna this time” on the second get together.

And then she had the “It’s not you, it’s me” conversation with you and here we all are.

One thing I want to point out: as harsh as this may sound, she’s actually paying you a compliment by having this conversation with you. She was making a point of doing you the courtesy of turning you down in person and respecting your time by being fairly upfront about things. Those are all generally good signs. A lot of folks would just ghost on you or pull the fade.

But over all: you were feeling it. She wasn’t. You two may not have been right for one another, you may have been at incompatible places in life or there may have been some crossed wires. But at the end of the day, both people have to want to turn the key and she just didn’t.

Unfortunately, the best thing you can do is take what you’ve learned here and apply it to your next date.

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: Short and sweet. I just want to know how unhealthy it is that my girlfriend continues to be friends with all these men that openly want to have sex with her.

Concerned

DEAR CONCERNED: Normally, this is the sort of question I’d pass over because there’s pretty much nothing here and one that usually gets a snarky one-sentence answer. But I decided to feature this one because, frankly, I get this question a lot and honestly, in a lot of cases the details don’t matter. Yeah, there’re questions of “have they actually said ‘Hey, Concerned’s Girlfriend, I want to part you like the Red Sea and plow you like a field’ or are you assuming this?” and “Have you talked to your girlfriend about how you feel?” but at the end of the day, this comes down to one singular issue:

Trust.

Either you trust your girlfriend or you don’t. That’s really it.

See, one of the things that everyone is going to have to get over is the idea that other people are going to want to f

k their partner. Some of those people may very well be their friends. Hell, those people may well be their close friends. Some may be secretive about it, never letting on that deep in their minds, they fantasize about getting some intense crotch-snuggles with your sweetie. Some will be faking being their friend in order to get there. Some will be quite open about it. And while it’s important to be open with your partner about how you feel about such things – letting them know that you might be feeling a little uncomfortable with the level of intimacy the other person is assuming or asking for, f’rex – the thing you need to keep in mind at all times is very simple:

It takes two to horizontal tango. Or to mambo with the mamba. To bring the Ark into the Holiest of Holies. To be banged in the butt by the Space Raptor Invasion.

So at the end of the day, the fact that dudes may line up for miles in hopes of getting into your girlfriend’s panties, Concerned, it doesn’t matter because no matter how much they may want to raid her tombs, it ain’t going to happen unless she wants to f

k them as well.

And don’t get me wrong: the fact that she’s hanging out with dudes who want to f

k her isn’t an indication that she is planning on – or wants to, or has even thought about – f

king them. Maybe she doesn’t know. Maybe she does and is willing to overlook things because he’s not an a

hole about it or because their friendship has always been flirty and that’s just their dynamic, or she knows and really wishes he’d drop the subject because otherwise he’s a decent guy or she knows but he’s never said anything so she’s willing to pretend she doesn’t know.

Now, maybe she does know and likes stringing those guys along. In which case the problem isn’t her friendship with those guys, it’s her personality, and you’re better off breaking up with her because Jesus, who wants to deal with that bulls

t? But the likelihood of that is so damn rare that you may as well buy some scratch-offs while you’re at it because if you beat those odds, you might win $75,000 at the Circle-K.

But back in the world where women aren’t conniving, Machiavellian schemers who mostly exist in the fetid and fedora’d imaginations of guys who they’d never date in the first place…

You don’t get to dictate who your girlfriend is friends with or under what conditions she’s able to be friends with them. Either you trust her, or you don’t. If you do trust her, then it’s on you to use your words like a grown-up and ask for a little reassurance from her because right now you’re feeling a little insecure and you’d appreciate it if she could help walk you back from the edge. If you don’t trust her, then it’s time to break up with her.

DEAR DR. NERDLOVE: A few years ago I met a guy. I thought he was cute and we were both socially awkward. Two years ago we had an awkward make out session and that was the end of the crush, but we’re still friends.

I noticed after the make out session that he started getting kind of weird. I am pretty sure he’s a closeted transgendered individual. I kind of brushed off the signs like him always identifying with the female protagonist and his favorite shows being about people who felt like they were born in the wrong bodies.

Last year we went to a fan convention and he decided to dress up as a female character. When he asked me if he should do it, I told him to do whatever made him happy. I didn’t realize that by telling him to do what he wanted that it put me on the hook for having to emotionally support his decision.

He spent the entire convention making me do his hair and makeup. He asked me every five minutes if he looked pretty. He wanted to obsess about how his bra made him feel and how to avoid showing his underwear when he leaned over.

He also started a fake Twitter account where he pretends to be a girl. He will contact me to gleefully tell me that some guy is flirting with him because they think he’s a girl. He will ask me if I think this person is flirting with him and what should he say back.

I have never mastered the fine art of being a girl. I didn’t spend my teenaged years sitting around my pink bedroom with my friends talking about my period like the chick from “Are You There God, It’s Me Margaret.” I got sexually harassed and assaulted and consider it a miracle that I survived my teenaged years without committing suicide. I find it very difficult to get giddy and enthusiastic with this guy over things that caused me a great deal of shame and pain growing up.

Any time I try to make it clear to this guy that I don’t want to talk about make up and would rather go back to talking about Doctor Who like we used to, I get accused of being intolerant of his kinks even though he staunchly refuses to identify as trans.

I am trying to be tolerant. I think people have the right to do whatever they want to, but that includes me too who doesn’t want to spend days assuring a guy he looks pretty while he talks about how the underwire from his bra is digging into his chest.

I don’t know what to do. I don’t have anyone to talk to about this because he made me swear not to tell any of our friends he is doing this. I told a friend about it and she told me to keep it to myself because it would make me look bad to tell anyone that this guy is doing these things. I am incredibly depressed and upset and don’t know what to do.

Thanks.

Reluctant Girlfriend

DEAR RELUCTANT GIRLFRIEND: Whether your friend is trans or not is beside the point. The problem is that, cis, trans, non-binary or just kinky, your friend is kinda being an asshole. It’s one thing to be excited about something and really want to discuss it with a close friend. It’s another entirely to get pissy at someone you’re (general you, not you, RG) friends with and manipulate them into only talking about the things you want to talk about by insisting that they’re a bad person because maybe they’d like to talk about something else for once.

You’re right: the fact that your friend wants to talk about their crossplay or make-up doesn’t mean that you have to as well, especially if that’s something that makes you uncomfortable. Friendships go both ways; you’re allowed to have preferences too. Pulling the “you’re kink-shaming me” card is a manipulative and s

tty thing to do to someone when all they want to do is change the subject.

If this is them getting taking baby steps towards getting comfortable with their gender, then hey, more power to ‘em. It’s important to support your friends in times of crisis or confusion. But being a supportive friend doesn’t mean you don’t get to have boundaries, nor do they get to run roughshod over yours. This is a case where they’d do better to find someone who IS interested in talking about this. Not every friend in somebody’s social circle needs to share ALL of their interests or talk about ALL of them at all times.

So what do you do? Well, if your friend refuses to acknowledge your stated preferences and discomfort and tries to guilt you into playing along anyway… you break up with them. You can – and should – break up with friends, especially if they’re being s

tty to you. The fact that they may or may not be trans doesn’t give them a “get out of being an a

hole free” card, nor does their circumstances (whether their coming to terms with their gender identity or just discovering that they’ve got a specific fetish) mean that you’re handcuffed to them like you’re in The Defiant Ones. You’re allowed to stop being friends with someone for pretty much any reason, really. You’re not on the hook to manage their feelings or be their personal sounding board and cheerleading squad.

So let things end. It doesn’t have to be a big blow-up; you don’t have to make a production over dumping them as a friend. You can just as easily let things dwindle away – as friendships often do – by being less and less available if you prefer. But either way: give yourself permission to end the friendship. They can find someone who does want to opt-in and talk about make-up and boys and pretty dresses and you can find your fellow Whovians who want to come up with head canon about how Attack The Block is the time the Doctor met up with Finn from Star Wars and also how we really don’t need any more episodes about giant spiders, ever, thanks.

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: Recently I have been frustrated, solely with myself. Because in the last few years I’ve lost 40 pounds, made impressive strides in my career for a man my age, and went from not being able to talk to anyone to making classes/groups of people screech in laughter. I say I’m proud of myself because I am, but there’s one last hurdle I need to get over and I’m hoping you can provide perspective.

Women who I consider beautiful, and who I want to sleep with, try to sleep with me, and I freak out (yes I’m a virgin). One of two things happen:

1. I completely begin over-analyzing and ask myself  “Do I want a relationship with this person? Or just casual sex? Will I ruin my chances if I have sex now?” I basically twist myself so backwards that by the time I have made a decision, they have completely moved on.

or

2. I panic and just straight up say “no”. Even when I mean yes! I will admit it stems slightly from a fear of performance, but I’ve been really working to overcome that and don’t really feel like that’s the main problem.

When I take a step back and analyze the situation I walk away with this conclusion: I don’t know if I really want to have sex with someone because I don’t really know what sex is, as stupid as that sounds. Of course I know what it entails physically, but not what it entails on an emotional level.

I know the standard narrative is that men are pressured to have sex with anyone as soon as possible, but I feel as if that’s been reversed. All my good pals tell me I should wait for someone special, but in all honesty I’m horny, and I feel like I’m being pressured to wait for this completely unrealistic fantasy that’s never going to just walk into my life. I want to have the physical act of sex so I can grow and learn emotionally, therefor when someone I do really love comes into the picture I won’t panic like I do right now.

To sum it all up Doc, should I have sex with someone who I do like, but know I won’t end up with in the long run, or am I wasting a valuable emotional moment in my life? Because to be honest the lack of sex has really been dragging on me mentally, I will not say I’m depressed, but I do have some serious slumps sometimes. I get distracted, I become angry at people who I love, and I can get easily agitated at times. These aren’t horrible situations compared to others but I feel like I’m suffering and having anxiety all for something completely natural that people do everyday.

Sincerely,

Dude Who Wants Some Wisdom

DEAR DUDE WHO WANTS SOME WISDOM: First of all: congratulations! You’ve made a lot of progress in your personal development and you’ve taken major strides to become the man you want to be. That’s impressive, and you should be proud of yourself for what you’ve achieved. Which is why it’s kind of a shame that you’re hobbling yourself with these self-limiting beliefs.

I realize that I say this so often that it’s basically a cliche around these parts but… dude, you are seriously overthinking this.

There’re a couple things going on here. The first is that you are dealing with a particular kind of performance anxiety. Normally when I hear from virgin men who are worried about their first time, they’re worried that they’ll be lousy in bed and this reputation will somehow follow them to every woman they’ll ever be interested in… even if she lives in an entirely different city and has absolutely no connection to anyone he’s ever known.

Because women are a telepathic hivemind, I guess. Don’t ask me to explain it, anxiety is never logical.

You, on the other hand are worried about what having sex will do to you. Will you set yourself up for a loveless life because you didn’t have a perfect first time? Will you have ruined your chances of dating someone — either that person, or some person to be named in the future – because you had a casual hook-up? This is getting you so twisted in knots that you’re freaking out over the possibility of banging someone.

The other thing is that you’ve bought into the cultural idea that losing your virginity Means Something. That you should wait for Someone Special — ideally someone you love or at least who’ll net you major props from others for having your first time with them — and have some magical, meaningful experience. Whether it’s the typical right-wing Christian idea that you’re only ever supposed to have sex with one person, ever, or that someone choosing to have sex with you means that you have value, there’re a lot of messages out there that sex has meaning and impact and you need to manage it carefully lest something bad happen. Bad things. Very bad. Don’t ask, they’re so terrifying nobody can really explain ’em to you.

Here’s what losing your virginity means: it means you’ve had sex. That’s it. Everything after that is what you bring to it, not anything inherent to the act itself. Virginity isn’t a state of being, it’s just a case of having never had a particular experience. I’ve never jumped out of a perfectly good airplane, but letting that define who I am as a person would be absurd, as much as believing that doing so would lead to massive changes in my life. After you’ve lost your virginity, you will be the exact same person you were before. The only way it will change you is if you decide to change, a decision you could’ve made at any time. Like Dumbo’s magic feather, all this did was give you permission to unlock the potential that you could’ve accessed at any time, if you’d so chosen.

My recommendation for who to have sex with and when is: when you’re ready and with someone who is worth having sex with. In an ideal world, you want a partner who’ll be considerate of your inexperience, who you can communicate with openly and honestly and who is interested in making sure you have a good time. While you’re more likely to find that in the context of a relationship — romantic, friendship or otherwise — you can find casual partners who would actually be thrilled to be breaking in a newbie. Casual sex doesn’t mean being casual with people’s feelings, after all. So if you have someone you know who’s warm for your form and wants to hook up and you feel like they’re someone who’s worth sleeping with… if it feels right, then by all means, go for it. Similarly, if you decide that you’d rather avoid the question of “well, what if I might want to date this person,” then do your research, find a sex worker who specializes in what’s known as the “girlfriend experience”, tell her what you want and tip her well afterwards; an escort is far more likely to be conscientious of helping you have a good first time than hooking up with someone you just met at a party.

And incidentally: if we go strictly by statistics: the first person you sleep with is unlikely going to be the person you stay with for the long term. That has nothing to do with being a virgin or inexperienced, it’s just the nature of how relationships work. I know people who’ve been with one person their entire lives — and they’re happy as clams, don’t get me wrong — but they’re outliers, not the norm. So don’t let the potential longevity of the relationship be a major deciding factor.

The key isn’t to get hung up on What It Means. It means exactly what you want it to mean, nothing more, nothing less. That’s why it’s fine if you don’t want to date them, or you don’t know if you want to date them; having sex with them isn’t going to slam the door shut. I can’t count the number of relationships I’ve seen that started as one-night stands that just never ended. Similarly, waiting for commitment or what-have-you isn’t going to make things better or worse. If someone only wants to sleep with you, making them promise that they’ll love you until the end of time isn’t going to change their minds.

The thing to keep in mind is that just having sex isn’t going to make you grow emotionally or resolve your inner conflicts; that’s something you do for yourself. You can have had dozens of casual partners and still panic when you realize you’re in love with someone because Now It Counts. It’s all going to come down to how you choose to look at it. If looking at it as “something to get out of the way” helps you then that’s the best way to do it. If looking at it as “well, I’d prefer a relationship,” would be better for you, then you do you, king. Hell, you could decide you’d prefer a relationship, then take the opportunity for casual hook-up instead and that is just as right and valid a choice. Regardless of which way you decide to go: just make sure it’s someone worth sleeping with… which is my advice for whether its’ your first partner or your hundredth.

It’ll be fine, my dude, and once it’s all said and done, you’re going to wonder why you were so worried about it all.

You’ve got this.

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