I’m morally conflicted about having sex with my closest friend

aygurl asks: 

I genuinely consider myself a nice guy. I treat women with respect and when in love I would do nearly anything for them (including keeping them happy both emotionally and sexually). I’ve known this girl for a couple of years, I consider her my closest girl friend. We talk about nearly everything, we laugh and enjoy each other’s company. When I went off to uni we lost touch, but last Christmas we started talking again. We discussed our sex lives, I tell her about losing my virginity and about a couple other girl I’ve hooked up and slept with. She, on the other hand still hasn’t and rants about how sexually frustrated she is. So, I suggest a sex pact if she’s not taken by the time she’s 20. About a week later she calls me when rather tipsy and asks to bring it forward to now… I’m absolutely chuffed, not only will I get to have sex but she’s comfortable with me being her first. 

We plan where and when but it gets complicated and eventually falls through. We do however plan to do it in London, (she has a flat there and i’d fly down and spend the weekend). However, she gets cold feet JUST before I’m about to book my flights she calls me and said she’s had second thoughts and would rather lose her virginity if she was in love, so we call it off and just go back to being friends. In a way I was almost relieved. I respect that (usually) the first time, especially for girls, it’s suppose to be special and with someone you love and in a relationship with. 

However, now that summer is just around to corner we’ll hook up and the subject will probably come up again. The thing is I’m morally conflicted, she’ll want a relationship whereas I won’t. I respect her too much to just sleep with her and have nothing more because I don’t want to hurt her.

Whoa, this is A LOT to unpack. I hate to do this because you’re asking for help but I have to call you out. You’re not a nice guy. What makes you nice exactly? The fact that you’re a pushover? I’m always wary of anyone who describes himself as nice and then tries to quantify it by describing qualities that make them sound like a toady. Ladies, you should be wary of any guy who describes himself that way and then tries to illustrates his niceness by saying that he would do “anything” for you because what it really means is that his willingness to do “anything” for you, in his mind, trumps the fact that you might not be into him and this lack of attraction will be taken as a personal insult to him. Guys, if you’re reading this and consider yourself a nice guy, please note that the willingness to do “anything” for a girl is not the way to go through life. Being a pushover is never, ever, sexy to a woman. Remember that. I love my girlfriend but if she suddenly asked me to do something that was reprehensible to me, there is no way I’d do it.

Now that we covered that, here’s your situation without all the double talk:

You have a friend who you’re attracted to. You’ve discussed sex, she tells you she’s sexually frustrated and then you propose a sexual pact by the time you turn 20. She calls you while drunk and then suggests having sex sooner rather than later. You try to arrange a meeting but it falls through due to hesitance on her part. She tells you that she wants to wait until she loves the person she’s with before losing her virginity.

Looking at that situation, I’d immediately tell you that unless you want to commit to her, don’t bring up the sex talk again. She’s clearly looking for something you’re not. You don’t mention anything even remotely close to wanting to be in a committed relationship with her. In fact, your “pact” wasn’t even “Let’s date if we’re both single by 20” it was “Let’s have sex if you’re single by 20”. You clearly don’t want to date her, so don’t try to have sex with her. There is no moral conflict here. 

Normally I’d end it there but I REALLY need to address your last statements.

However, now that summer is just around to corner we’ll hook up and the subject will probably come up again. The thing is I’m morally conflicted, she’ll want a relationship whereas I won’t. I respect her too much to just sleep with her and have nothing more because I don’t want to hurt her.”

That my friends, is classic nice guy bullshit double talk. I respect her too much to try to just sleep with her, but I know the subject will come up. Really dude?  Firstly, since you’re clinging to this nice guy shield let me tell you something. You don’t have to talk about sex with her and you definitely do not need to hookup with her. I know, it sounds like a revolutionary idea, but you don’t have to hookup with people if you don’t want to. If you truly respected what she wanted, you’d tell her point-blank that you’re not looking for a relationship, and hooking up is a bad idea. The reason you’re having a moral conflict is because you think you’re somehow doing her a favor by hooking up with her but not dating her.

What you really were describing, was a dilemma involving your brain and your penis.  If you really want to be a good friend, don’t hookup with her. Or if you do plan to hookup with her, tell her BEFORE YOU HOOKUP that you’re not interested in a relationship. Do this while you’re both sober, maybe even over the phone, and put no pressure on maintaining the casual hookup aspect of your relationship.

Be a good friend, and try to focus less on being the nice guy.

Good Luck Out There.

Demetrius Figueroa

Demetrius is a sex, dating, and relationship writer based in Brooklyn.

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