Frenchie said 9 years, 6 months ago:

I’ve been fooling around with this guy–who is easily one of my closest friends–for about a year and a half now. We’ve never gone all the way, but he’s made it clear that he wants to have sex with me. We’re not in a relationship. I know that you don’t have to be in a relationship to have sex with somebody, but I’m worried about losing my virginity to a guy I’m not in a relationship with. I’ve been battling guilt and anxiety about our “friends-with-benefits” (I hate that phrase, but it’s fairly accurate in our case) situation since it began. For a while, I was comfortable with the way things were. I was trying really hard not to let my anxiety get in the way of that. I was having a very hard time last year, and those moments when I was with “J” made me feel better. That’s the worst part about not having a boyfriend, the cuddling. I miss cuddling, and “J” is always there when I need that. I suppose my real problem is that sometimes I’m concerned that I feel more for him than just friendship. And, if I’m being honest, I’ve suspected that “J” has other feelings as well. He only says things that sound more-than-friendly when he’s drunk, but I don’t know if that makes it more truthful or less truthful.
I suppose my question boils down to the aftermath of having sex. What if I regret it? What if it just amplifies my anxiety and makes me clingy? What if I fall in love?

raven said 9 years, 6 months ago:

Damn, these are crazy questions. I know I lost my virginity to some random guy. At first, I wasn’t pissed off… and then I became pissed off…but now I’m not. I kinda just let it pass. Maybe you should just take it one step at a time. You also may never know if he likes you unless you either ask him, tell him and see what he says or he makes it extremely clear to you. Usually, people say that if someone is drunk they tell the truth and in this case it might be true. If you fall in love, there is nothing wrong in that, however, if he doesn’t love you back you should think of yourself and move on. I believe you can always fall in love again if you want to. You have to be cautious in life, but not extremely cautious because you may end up missing great opportunities. Maybe you should set up some scenario where you end up telling each other that you love each other or something.

David said 9 years, 6 months ago:

Hi Frenchie, though I am a guy, I still think I can help you out a bit. From what you’ve written, it boils down to you not knowing if you will regret it, and if your actions require or will result in love. First of all, if the mood is right, you won’t regret it afterward. Depending on several factors, it will hurt (but if you want it then perhaps it is different). A first time is always exhilarating, the nakedness and so on, but it becomes a lot more meaningful if there is love involved. That is important. I would say that you that you should be romantically attached to each other before to reduce the regret probability. My ex wasn’t that romantically attached, and she regretted it, but learned to live with it and move on. It isn’t terrible if you regret, but it would be nice if you cherished the memory.

Just see if you can tickle his view of you out of him. If “J” doesn’t want friends with benefits but a proper relationship, go for it. You obviously know and trust each other, now you just need to solidify that. Also, you can talk about your feelings while cuddling: will be more likely to be honest since he feels comfortable around you. Just give it a shot!

Mellow Mallow said 9 years, 6 months ago:

I mean, part of the thing about aftermath is that you really can know the aftermath of something once you experience it. You can attempt to predict how you might feel or react, but with a new experience it’s impossible to know for sure.

My advice to you is to ask yourself this: do you want to have sex outside of a romantic relationship? are you comfortable with that? If you aren’t thinking a solid yes, don’t do anything. Find out whether or not ‘J’ is interested in a romantic relationship. Also ask yourself if you want to have sex INSIDE of a romantic relationship, and if you’re ready for that. Odds are if you’re not sure, the answer is probably no, you’re not ready. For myself, I waited until I was ready, and I have no regrets, and I’m really glad for that.

WanderingCreature said 9 years, 6 months ago:

If you already have anxiety about your friends with benefits relationship, then I don’t recommend having sex with him if you are not in a relationship.
HOWEVER
if you think you have more than just friend feelings for him, why not ask him out! then you won’t feel guilty about anything you do with him because you will be in a relationship :)
Good luck!