Skip Nav
I Never Thought I'd Allow Myself to Be in a Physically Abusive Relationship — Until I Was in One
Harry Potter
These Harry Potter Book Cover Illustrations Are Bone-Chillingly Beautiful
A Letter to the Mother-in-Law and Father-in-Law I'll Never Have

You Asked: Should I Sleep With Him?

Dear Sugar--

In a couple of weeks I'll be visiting one of my guy friends who lives out
west. The whole time I've known him we've had this sexual tension between us -- he's kind of my ideal guy -- but it's never been convenient, nor is it convenient now, for us to date. The last few times I've seen him we've gotten close to sleeping together, and I have a feeling the same thing will happen on this occasion. I wonder if it would be better this time to just give in to temptation, throw caution to the wind, and go through with it, or whether I should forget about sex entirely. I'm afraid whatever I do, I'll end up regretting it later.

--Contemplating it Connie

To see DEARSUGAR's answer

Dear Contemplating it Connie--

You've got to ask yourself why you are going out to see this guy in the first place. This sounds like a sexual escapade waiting to happen since you two have so much sexual tension built up. It's obvious that you have feelings for each other so why is it not convenient to date each other? Is it distance? If so, it may not be a good idea to start something knowing nothing can come of it.

On the other hand, if you are both in agreement that it's okay to be intimate with each other with no plans for your future -- no strings attached if you will, than it's totally up to you if you want to throw caution to the wind. I would advise you to have a chat about it first to make sure you are on the same page to prevent any hurt feelings afterwards.

I'm also wondering if you are you thinking about having sex with him because you wish you were together -- if that's the case - DON'T do it - DON'T even go out and visit him. Seeing him and having sex will only make you want him more, and unless you can make this relationship work, it'll only complicate things and make it harder to get him off your mind.


Join The Conversation
<3-Gossip <3-Gossip 10 years
In a similar position...Except we were in a relationship (prior to that we have known each other for 4 years)but we had to end it..Because we wont be able to see each other for a year and neither of us (Though we care very much for each other) want to have a long distance relationship..We will be in different countries. Feelings will most likely evolve if you choose to sleep with him.
trendyindc trendyindc 10 years
Ohhh you definately will want more (unless its awful). I have the same situation right now and my jaw dropped when I read this. Haven't done anything but I know that I want more and am willing to at least admit it to myself. Just take it slow because you can't undo it later.
junebrug junebrug 10 years
Only your heart knows the answer. Are you looking for a good time or a relationship with him? The second one is your answer, just say no.
Marci Marci 10 years
I wonder too why you're going to see this guy? Sounds to me like you've got the hots for him and are sort of hoping something *will* happen. But if it does, then what? You already say that it's not convenient for you two to date. But if you sleep with him, aren't you going to be wanting more from the situation afterwards? I kind of think you will.
kayden kayden 10 years
Clearly think this through, go with your gut feeling. It seems like you have a lot of anxiety about what to do. Don't do it if your setting yourself up for failure. You should be happy in your relationship. Starting a relationship on doubt is wrong.
popgoestheworld popgoestheworld 10 years
Sounds like you two have had fun messing around in the past - no need to take it to the next level if it's not something you are comfortable with.
cgmaetc cgmaetc 10 years
Consider the flip side: what if you hookup and it's awful? I was in that situation once. I built up this guy in my head, we had all this sexual tension, and when we finally did the deed, I was sorely disappointed. Worst sex ever. But the guy was sprung on me. He wanted to be with me and I tried to keep him as just a friends. It took me 3 years of ignoring his many phone calls and emails for him to get the message. Just because there is (sexual) heat, doesn't mean there's a fire!
Natty Natty 10 years
if you are worried about regretting it later either way. do not have sex with him. you are not ready to change your relationship. when you have sex with someone you can't be worried that you will regret it. have fun visiting him, and make sure that you are 100% confident in what you decide. once you have sex, you can't take it back.
Anal Sex Tips
Negative Effects of a Sexless Marriage
Are Passion Dust Glitter Vagina Bombs Safe?
Am I in Love?
From Our Partners
Latest Love
All the Latest From Ryan Reynolds