I learned this lesson the hard way when I started dating a friend in high school.Not only were we good friends, but our families were also extremely close and had been for years.

Kelly: Well, you spend as much time together as you possibly can, eventually you get irritated for pretty much no reason. One of our goals this year is to spend more time with other people because we need that to avoid some of those moments when we’re staring at each other and thinking, “OMG, GO AWAY!

Ashley: We sometimes get stuck in our little bubble, just seeing each other, just talking to each other, just hanging out together, and it’s fun for a really long time. ”Kelly: Talk to your friend, see how they feel, and go from there.

Kelly: I believe we handled the evolution of our relationship very consciously.

Nothing felt weird to me, but the transitions didn’t just happen on their own.

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.

And we introduce each other to new things all the time.

Plus, he’s fun to talk to about anything because he’s animated, opinionated and hilarious.

We sought each other out, dated, then became friends. We’d find ourselves in the same city – Los Angeles, or Paris – because of our work, and we’d catch up.