Hello Doctor,

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.


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.

Just a 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.

Good luck.

Dear Dr. NerdLove,

Stop me if you’ve heard this movie pitch before. Male in a long-term relationship with girlfriend falls for his female best friend. Well, it’s not a movie anymore, it’s my life and I need your advice.

I have been in a relationship for over three years now. Unfortunately, due to our respective working lives, my partner and I have spent very little time in the same place for any significant length of time. As you might suspect, this has been a source of some strain over the course of the relationship. We’re both pretty understanding and accepting but we’ve missed out on a lot of relationship development. Stuff that couples who spend time together get, i.e. shared experiences.

Enter my best friend and observe – like a magnificent Bob Ross painting, here is where the elements truly begin to come together for you.

My best friend has been on the scene for about five years now. Early on in that friendship, I went through a separation from a looong relationship (over 10 years). Dare I say it, then ‘just’ friend and I acted on some feelings. It was short-lived (my fault) as my then-recent ex was still in close proximity and that whole space of my life was one big maelstrom. I ‘cooled off’ as I tried to sort that side of things and my friend and I didn’t take it any further. Eventually, she moved on with someone else.

A year on from that separation, I met my partner and we started dating. Some 6 months or so after this, my friend and her then partner split in a pretty bad way. I can’t remember the precise words, but I do remember her then lamenting about the timing of her breakup and my new relationship.

We carried on as friends and eventually, best friends.

In June this year we were attending an event with friends and (seemingly) out of nowhere I had this pang of immense sadness and guilt. I realised that I enjoyed the time I spent with my friend more so than I did my own partner. She saw the pained look on my face (apparently, I was more outwardly affected than I thought) and asked me if I was okay before commenting, ‘you look like you’ve made a terrible mistake’. The irony.

I tried suppressing that and putting it to the side but then in July we were at another event with mutual friends. There, someone from outside our friendship group who we had only known a couple of hours gave some unwanted relationship advice. Basically, they took it upon themselves to tell us each individually that we needed to stop treating the other like a partner and to move on. It was not the first time we’d been ‘mistaken’ as being partnered by others, but it was the first ‘attack’ on the nature of our friendship. I want to be clear here, we’re not physically intimate/affectionate or anything like that, people just seem to get ‘a vibe’.

Those comments got in both our heads and for a brief time our contact was ever so slightly strained. I brought it up, we both acknowledged that things had gone weird and that the ‘advice’ seemed to have been the trigger. After that, things kinda went back to normal. Kinda.

In the last month or so we were at ANOTHER social gathering when one of the attendees suggested that she date one of the other attendees. Holy Raptor Jesus… an absolute torrent of jealousy crashed upon me. I had never experienced something quite so profound. It shocked me and honestly left me disappointed in myself as after all, whom she dates is none of my business. Still, I ended up excusing myself and retreated to the bathroom to re-compose. I felt ill.

That hasn’t really subsided and since then I’ve been trying to work out whether I should be doing something about what I’m feeling and if so, what should I be doing.

I feel like I’m letting them both my partner and my friend down in a serious way. My partner has done nothing wrong in all this and we have recently spoken about and made plans to spend more time together to build on our relationship. On the other side, I feel like I am at risk of impeding my friend’s potential happiness and/or otherwise opening a can of worms that will jeopardise our friendship. Basically, I can’t tell the future and I’m afraid of the consequences.

I would be grateful for your wisdom and thoughts.

Yours Sincerely,

Corny Rom-Com

So before I get to my question for you, I want to point out that attraction in and of itself doesn’t mean anything. Crushes happen; they have absolutely nothing to do with the status or strength of your relationship or your feelings for your partner. Being attracted to another person, having a crush on them or even getting jealous that they might date someone else just means you’re a person with eyes and a sex-drive. Sometimes it’s a slow burn, sometimes it hits you with the suddenness and impact of a car crash out of the clear blue sky, but they happen. The key is to recognize that they don’t have any serious meaning and they don’t mean that you need to do anything about it. You can just ride that wave and enjoy the giddy feelings that come with it without trying to make it more than it is; crushes tend to fade on their own.

It’s not surprising that you have complicated feelings for your best friend; you’ve got history together, you’ve spent a lot of time together and it’s pretty clear that you two have some serious chemistry. It’s completely normal, not something to freak out about.

Now here’s where things get tricky. You know how I said that your being attracted to someone else doesn’t mean that there’s anything wrong with your relationship with your partner? That doesn’t mean that there couldn’t be problems in your relationship that exist independently of your feelings for your BFF. It’s possible that your feelings for her are just making it harder to ignore those issues.

So that brings me to my question for you, CRR, and I want you to be honest with yourself if not me: do you want to fix your relationship with your girlfriend? If your best friend didn’t exist, would you still want to be in this relationship? Because the way you write about it makes it sound like you’re in it because… well, you’re in a relationship and this is what you’re supposed to do. The way you describe the early stages of your relationship together sounds like a long-distance relationship without any of the good parts. It might be that this just isn’t a relationship that’s working for you. Compatibility has three factors: right person, right place and the right time. Someone can be the right person for you in other circumstances but they may not be in the right stage of life, the right physical location or in a place where your lives simply don’t mesh correctly. If the timing doesn’t line up, all the sincere intentions and desire to make things work won’t change things. It ends up being like gears grinding against one another instead of synching like a well-oiled machine.

Recognizing this doesn’t mean that you’re betraying them or doing something wrong; it just means acknowledging the reality that things aren’t working for you. There’s no good guy or bad guy here, just unfortunate victims of circumstance.

Now, notice very carefully that I haven’t said anything about your best friend in all of this. These are two separate issues and need to be handled separately. Right now, you’re conflating the two and it’s making everything difficult. You need to put your feelings for your best friend aside as though she didn’t exist — kill the Buddha, as it were — and consider what you want for your relationship with your current girlfriend. If you come to the conclusion that you’re holding on to the relationship more out of a sense of duty or inertia — trying to make up for the shaky start you two had — then it’s better to sort that out first, without looking at your best friend as the prize at the bottom of the cereal box. Similarly, deciding that you do want to make this work means putting those feelings aside and giving your relationship your undivided attention.

Once your status with your girlfriend is resolved, then you can decide what you want to do about your feelings for your best friend — if anything. You may realize that they’ve faded and you’ve gone back to being friends again. You may decide that you want to talk things out with her and see how she feels and the two of you can decide if you want to try giving being a couple another shot without the drama of your ex lurking in the background like Banquo’s ghost at the feast. Or she may have started another relationship and you’ll have to take this opportunity to make your peace with the fact that once again, right person, right place and right time didn’t line up… which sucks, but it means that you can draw a curtain on that particular stage of your life.

But the thing to keep in mind: being attracted to someone, even asking them out on a date, doesn’t mean that you’re going to ruin your friendship with them. The thing that ruins friendships is not accepting the friendship. If your being friends is always going to be a referendum on your feelings for her or you’re never able to let go and be happy for her when someone else makes her happy… that would be what fucks things up for the two of you. That doesn’t mean you can’t have a sad for what didn’t happen… but you need to be able to accept it, let it go, and appreciate your friendship for what it is, not for what you hoped it would be.

None of this is easy. You have some thinking to do and some questions to answer for yourself. What you shouldn’t do is be down on yourself. You’re not betraying anyone, you’re not letting anyone down. You’re just dealing with two relatively complicated situations that, unfortunately, happened at the same time. None of this means you’re a bad person, you’re just a normal person in an uncomfortable situation.

It’s rough, but it’s not unmanageable. You’ll work this out. I promise.

Good luck.

Previously published on and is republished here under permission.


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