When we broke up nine months later, all the usual post-breakup awkwardness and bitterness were multiplied tenfold by the fact that we were forced to hang out whenever our families got together, which was often.

On the flip side, when we rekindled the flame after college, our friendship and the friendship between our families became one of the best parts about our more-than-friendship.

I’m booking a flight to New Orleans for this weekend. Brice: I should have been with Maggie since ’08, but then again, I suspect I am better because of the experiences in between. A decade of dating in NYC can teach you a lot about yourself.

Ashley: No matter where I am or what I’m doing, if I’m with Kel, we can turn it into a good time.

We don’t just like each other, we also like A LOT of the same stuff.

He made me laugh a lot, but I was very suspicious of him. And he was a white boy with a slight country accent who drove a pick-up truck.

I assumed he’d be more into a woman who reminded him of Taylor Swift.

We had a shared history, our siblings adored each other and we even went on a few joint-family vacations.

Having personally experienced both the positives and the negatives of dating a friend, I’ll say this: there are few things more precious than a friendship that becomes more than a friendship, but there are also few things more painful than losing a romantic relationship and a friendship simultaneously. To commemorate the end of Friendship Month at Man Repeller, I interviewed five couples who braved the stakes and went from “friends” to “more than friends.” Below, their thoughts on what that leap was like.

Also, if your friend doesn’t share those feelings, don’t be angry with them. I would have liked it to be more then, but it wasn’t, so we became friends. Brice: I always harbored a greater appreciation and respect for Maggie than “just a friend.”Maggie: The best year of my life. The company had just gone through some big milestones and I was totally fried. The moment we saw each other – we hadn’t seen each other in a while – it was on. Of being alive.’ It was real life, better than I could have imagined.

(So far.)Brice: We could say we’ve been together for a year, but we could also say we’ve not been apart for eight or nine or 10 in many ways. Pretty much out of the blue, he said, ‘Look, I need to get out of town. It just made total sense, and was a complete surprise at the same time.

Kelly: We were good ol’ fashion friends from the fall of 2010 to the fall of 2011. Then we were friends with benefits until I moved to Seattle, and then back to just friends until October of 2013.