6 Brutal Truths About Having A 'Friend With Benefits'

To sleep with or not to sleep with? That is the question — at least the one that runs through the mind of any single gal with a great guy bestie. An admittedly far stretch from its Shakespearian derivative, you've got to admit that this question requires some serious thought.

He already puts up with your obnoxious Nashville obsession, listens to you bitch about co-workers, and makes a mean bacon egg and cheese... why wouldn't you have sex with him? It worked out well (in the end) for Justin Timberlake and Mila Kunis in Friends With Benefits, but we all know that's not always the case.

Here, six unattached 20-somethings dish on a time (or times) they decided to blur the lines between friends by knocking boots.

1. It can be a vaulable lesson in sex ed.

I'm sure there are tons of searchable quotes out there insinuating that the best friendships are the ones that you learn from, but I bet that none of them are referring to circumcision.

When Jamie realized that she and her guy friend Ben shared similar sexual appetites, she decided that it was worth a shot to invite him to visit her at school to see where the night took them.

"I instantly regretted it," she said. "He danced to house music in the bars like he was at a ska concert, and was clearly more interested in getting a taste of 'the college experience' that his small university was lacking than hooking up with me."

Rather than chalk the whole visit up as a loss, Jamie went for it anyway and ended up getting a lesson in sex-ed rather than getting off.

"It was the first time I'd seen an uncircumcised penis," she said. "After he left, I was suddenly repulsed — not by his penis, but by his personality and the night as a whole. And I actively avoid his texts and calls to this day."

2. Every f*ck-buddy has an expiration date.

You better take that into consideration before getting it on with someone you can't imagine your life without. Karen began hooking up with her friend Chris last April, who introduced her to a new sexual experience, and eventually, feelings of attachment.

"The first time we hooked up, I told him that I had never had an orgasm from having sex, while we were having sex," she said. "He quickly let me know that I was about to learn." Turns out, he was right, and she continued learning all summer long. "I lied and told him and his friends that I didn't have feelings for him, and that it was strictly business, so to speak," she said.

Despite her growing attachment to him, the two continued to hook up ... until she found out that he was dishing about their sexcapades all over the place.

"He told all of our friends that I squirted, and now they refer to my vagina as 'The Holy Grail' and have nicknamed me 'Squirtle,' after the Pokémon character." Yeah, consider that friendship (benefits or no benefits) officially over.

3. It's possible to maintain the friendship after the sex.

The first time that Steph and her best guy friend moved past their usual PG-13 make out sesh, she learned that mid-blowjob giggles aren't exactly a turn on.

"I couldn't help it! I was going down on him and I laughed because I just thought it was so funny, which apparently made him nervous," she said. "I told him I wasn't laughing at him, I was laughing at the scenario, but it didn’t change anything."

Needless to say, she never ended up finishing the job, but the two still maintain a great friendship outside of the bedroom.

4. Developing feelings will probably happen.

One of the best parts of a FWB relationship is that anything goes — as long as both parties are on the same page.

"I had been hooking up with my best friend for about ten months, but the words 'friends with benefits' didn't truly line up for me, because even though I wasn't looking for a relationship, I couldn't help but start to really like him," Bree said. "He always made it clear that he wasn't looking to date me, but then would drop lines like 'I love being around you,' and 'You always make me laugh'.

Eventually, I had to tell him that I couldn't keep hooking up with him if the relationship was never going to amount to anything. He told me that he loved me as a person, but couldn't commit the time to a relationship for academic reasons. As if he would magically begin to fail all of his classes and get kicked out of school if he were to become my boyfriend..."

Breanne saw through the excuses, but keeps up a platonic front.

"We agreed to remain friends, but I won’t hook up with him anymore because I'm not about giving myself up to someone who claimed to really like me, but not enough to date me."

5. It's best to not sleep over.

"This September, I stayed over a guy friend's house after a long night of drinking, even though I knew I had to be up early to go to a football game with friends the next day," said Ashley. She woke up around eight, with a horrible hangover, and decided to go back to sleep instead of going with her usual plan: sneaking out the closest exit.

"When I resurfaced around noon, he wanted to have sex again, so we did, and he dropped me off an hour later," she said. For some reason, their sober morning romp wasn't as much fun as their usual alcohol-fueled hookup. "I'm not upset that he doesn't like me like that, but after he dropped me off, I sat by myself watching the game — alone, still in my clothes from last night, and sore from sex," she said. "Not the best feeling."

If a potential hook up presents itself in their friendship's future, she isn't turning it down altogether, but definitely won't be sticking around for the morning edition. "And I'm never staying past nine at any guy's house again. Nothing good happens after 2 AM? No. Nothing good happens after 9 AM."

6. Respect is key.

Danielle and Ryan have managed to sustain a successful FWB relationship for over eight years now.

"It all started when I was in high school and bought him as a date for the senior auction," said Danielle. "I started hanging out with him and his friends all the time, and we just kept it going." A few years ago, Danielle put their friendship to the ultimate test by dating Ryan's best friend. "It was all fine. He was able to hang out with the both of us, without it being weird somehow."

Their secret? They value each other's relationships. "He respects who I'm with, and I respect who he's with, because at the end of the day we respect each other," she said. "If neither of us is seeing anyone, we just add hooking up to the mix, because it's easy and fun."