Lucky People Who Have Gone From Friends With Benefits To Dating Share How They Made The Jump

We've all hooked up with a friend here and there, but sometimes, the hookup goes far beyond the one time. It doesn't always end well, but the stories behind how friends earned their benefits are always a hoot. And sometimes they're hot.

PM_Me_Ur_Boobs_Honey asked, People who have friends with benefits, how did you go from friends to friends who have sex?

Submissions have been edited for clarity, context, and profanity.

This is one of the oldest tricks in the book.

Started as friends, ended up becoming roommates, both of us had been out of relationships for a while so sexual tension got high with us living together, slept together a few times and then she got a boyfriend so we ended things. We're still great friends, didn't ruin anything between us, it was just casual sex between consenting adults.

Screw it, why not?

We were at her place talking about Halloween. A very paraphrased version of the conversation:

Her: it's just an excuse for people to dress slutty and have sex

Me: sex is good

And then we had sex

Then there's the more direct approach.

I had been friends with D for years. I was dating her best friend K during that time. After K and I broke up, I stayed friends with D. We hung out a lot and one night she said 'we should still be just friends, but friends who have sex sometimes.' It was great and lasted for years off and on. We are still friends, but she's married now


One of my brothers screwed many girls while he was in high school and beyond. Eventually got married, and it just so happens that two of his best friends from college ended up marrying girls from his high school that he slept with. One time he told me that it makes him very anxious every time they're all out to eat.

Netflix and chill but with a little more class...

I was random friends with C. We had met through a mutual connection. One night after we had been texting for weeks and being friendly I jokingly told her I could show her how to make Carbonara...... I brought two bottles of wine, we cooked together... watched some stand up comedy and then ended up having sex. We were on and off since then and it was great~ we both date other people and occasionally hook up.

Ah the old "it's ok I'm here" ploy. "Brad" is a slick one.

Currently still have a FWB of 3ish years. "Brad", was the brother of my best friend "Kate" through high school and college, so we knew each other very well. I had just gotten out of a very bad relationship and was still in the "I'm going to cry and eat ice cream" phase when Kate invited me to a house party.

I ended up hooking up with Brad after the party. It was awkward for a little while after but then we started hanging out again and realized we could be friends who just happened to mess around if we were both single. It's been a fun arrangement.

How come I never get emails like this from real people?

Oh, let me quote the email I got out of the blue one day.

"If it wasn't apparent, I'm very attracted to you, and I think we could have really hot sex. I don't know if you're interested in adding the benefits package to the standard issue friends arrangement, but if so, we should talk about it!"

We talked about it. Then we started having sex. :D

Back-up/emergency d_ck is rarely disappointing.

We weren't really close, more like we had a mutual friend and added each other as a result. I'd known for years he'd wanted to sleep with me me, (he was very upfront about it, but respected my boundaries) but I didn't do anything about it. Few years later, I'm out of a relationship but I miss sex. He's randomly in town. I send him a message, we meet up the next day. F_cked off an on for a couple of years. Only regret is not getting it sooner.

Telling men they smell good is a great tactic.

I told him he smelt sexy (a mix of aftershave, whiskey, and cigarettes) and then he kissed me. Then we had sex and have been having it on and off ever since. No romantic interest in him whatsoever.

I always had a different image of sword-fighting...

I invited him to my room to play with the samurai swords he'd given me. Then pretty much just asked if he wanted to stay the night. He told me later that he'd just expected to make out, instead it turned full-blown Caligula.

We had crazy animal sex for almost a year. It ended because neither of us knew how to just keep it at sex-friends (dates, presents, spending the holidays together, etc) but he also didn't want to be in a relationship. So that was fun.

Practice makes perfect...

I had a friend a couple years back. We were both in college and kept in touch despite being a state apart we talked weekly. Well over spring break while we were both home he mentioned he recently lost his virginity and was told he was bad at it. I jokingly said well then we should practice to make you better. After talking about it and said we would just be friends with benefits. We "practiced" all summer and come fall when he went back to school that was the end of it. We don't talk about it anymore but I will say his girlfriend thinks he's great in bed and I'd like to think that was because of me;).

There really is something to this direct approach.

We were friends for about 5 years at the time and she was somewhat freshly out of a relationship of 6 years. We were just hanging out and talking about random stuff and she brought up thinking about using her time being single for the first time in her adult life (she was 25) as a reason to experiment a bit.

I gave her a sideways look for a bit and it went like this:

Me: I uh... wait... do you mean...

Her: Yes, pickalock, use your words.

Me: Oh, uh... no... I just thought you were trying to say something.

Her: What did you think I was saying?

Me: Oh, I thought you might've been hitting on me for a second.

Her: I was.

Me: Oh.

Turns out she's had a crush on me for.. well, 5 years. And cut me some slack. I'm 26 and while I've dated a couple of women, I've never actually had somebody outright tell me they had a crush on me before. Or even hit on me. It was a game changer.

We're back to just friends now (somewhat sadly). But much better friends, honestly. We both got to experiment and had a great time doing it.

If I had a dollar...

We literally hooked up at a party, had sex within an hour of meeting each other, and that's how we became friends.

Gonna need another dollar. Be careful with this tidbit though.

Get a boner, don't hide it, works every time.


Step one: be hot

This concludes how to get friends with benefits

Some people are really spoiled.

We dated for about 3 months but it fizzled out after he went on holiday and then I went on holiday as he returned, and we never picked it back up. Occasionally when we were drunk after that we would hook up and it was all okay. So sober I thought "why not?" and he was into it. We were FWB for like a year and a half until he got a girlfriend, now they've split up and we're having sex again. We've never had any feelings confusion (so far) in the two and a half years we've been friends (with on and off benefits).

The long goodbye is cute.

I liked a girl, we both knew I was moving relatively soon, and I made a move. We had some good times and we liked each other, but it wasn't fair to either of us to start something real knowing I wouldn't be around in a few months. But we had a fun few months.

And here's the lesson from this thread.

Just ask.

I have had sex with more of my friends than not. Individually, threesomes, foursomes with mates wives and my partner.

It's more people are afraid to ask or think it's wrong. Honestly, people just like to f***.

Image by Jill Wellington from Pixabay

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