For Glamour, by Suzannah Weiss.
Falling in love with and then subsequently dating your best friend is obviously a well-worn rom-com trope, but can it ever actually work out IRL? Sure, your significant other is supposed to be your best friend, but some buddies never pursue a romance out of fear that they’ll break up and ruin their relationship in the process. Things can get tricky in a hurry.
To see how friendships-turned-romances really play out, we asked women what actually happened when they dated their besties. The results are surprisingly mixed (and occasionally hilarious):
“It ruined our friendship”
“I dated someone I was close friends with in high school from my senior year of high school through my junior year of college. I wish we never did because when we broke up, even though it was amicable, I lost someone that otherwise could have been a friend for life. He was a really special person, and although it wouldn’t have worked out romantically, I would give anything to go back in time and keep him as a friend.” —Jessica, 29
“It ruined other friendships”
“Our relationship grew out of a very close friendship, and for a little over a year, it was wonderful. It seemed like the perfect idea: date an already-close friend. The trust is already there, you already have the structures and habits in place for hanging out together, and adding sex into the mix is just a bonus. But then it went bad. Awfully, horrendously bad. Initially, the problems stemmed from the slow-burn of our relationship and the fact that we never really sat down and defined what we were doing. Were we dating? FWB? We had different expectations for the relationship, and from there, we were doomed. The unhappy ending to the story is that both of us lost friends over it. Of our mutual friends, there was a clear delineation of who stuck with him versus me, and there has been little to no crossing of the aisle.” —Meg, 27
“A different side of him came out”
“After just a couple of months, he seemed to become a different person from the friend I’d known for so long. He became incredibly possessive, wanted to know where I was at all times, and discouraged me from leaving the house without him. He started talking a lot about ‘when we get married and have kids,’ while I was thinking, get me out of here. Over the course of a few months, I tried to improve things and even suggested counseling, but those attempts only made things worse, and he escalated to hacking into my email to read the messages I was sending to my best friend, in which I detailed my concerns and fear about his behavior. He went into a rage, accused me of betraying his trust by confiding in her (hundreds of miles away), and told me to leave. I blocked him on social media and email, and it’s now been five-plus years since we had any communication.” —Chelsea, 37
“The sex was awful”
“When we finally hooked up, the sex was so bad that I could barely stand to look him in the face. I tried to break it off — without mentioning the reason why — and over the next week or so he reached out to me with several desperate text messages, saying that he thought we ‘had something real’ and didn’t understand what had gone so wrong. We would often run into each other in our group of friends after that, so it took all the acting chops I could muster to keep our mortifying hookup a secret from everyone else, including his ex-girlfriend. I still occasionally run into him, and to this day I’m always so mortified by the whole thing that I can barely talk to him.” —Christine C.
“The relationship didn’t last, but the friendship did”
“We broke up but remained friends because we had that previous foundation.” —Kat, 32
“It lasted two days”
“We dated two days before I became positive I was a lesbian, then we stopped communicating at all because he was in love and shit.” —Tanya, 28
“It lasted five years and counting”
“We were friends for a year. We dated for four and a half, then broke up for six months. We’re back together again, and I’m pretty sure this is forever (for now). Marriage is in the future and that feels pretty weird. Can’t wait to raise puppies and live in the desert.” —Cassie, 23
“We became a power couple”
“We fell madly in love, moved from NYC to Detroit, and started a company together. We are still together and happy after three years.” —Alex, 26
“We lived happily ever after.”
“I married him.” —Stephanie, 26
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