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Still from the L Word with Shane and Jenny
Still from the L Word with Shane and Jenny

Is it worth the risk to move from friends to lovers?

The Bravo television show, Friends to Lovers asks: Can friends become lovers? As lesbians, when it comes to dating, it seems like our dating pool is made up of our friends. We tend to have very loose boundaries when it comes to dating – our exes are our closest friends, we date our friends, and sometimes even our friends’ exes.

I know, I have been guilty on all counts. And for me personally, each of them was a complete disaster and ironically those relationships became the most toxic relationships I have ever been in. Now I’m not all ix-nay-ing-on the dating friends-bay, but I made one key blunder. The mistake I made was this: I never considered whether the person met my criteria for a girlfriend.

It’s like because we were friends we skipped right over the “are we compatible?” conversation. In the end, because we had built trust as friends, I ignored what would normally be considered blaring red flags when it comes to relationships.

For example:

  • she had an untreated drug or alcohol problem
  • she cheated on every previous girlfriend
  • she would disappear for long periods of time and not return calls or texts
  • she couldn’t take a joke
  • she blamed all her exes for the relationships ending
  • she was financially unstable
  • she had no friends
  • she was super secretive
  • she wanted me all to herself, even as a friend
  • she was all into me until we became more than friends
  • she was open and communicative – until we started dating

Given my massive date-my-friends mistakes, I created questions to ask myself before EVER dating a friend again. If you’re considering dating a friend, ask yourself these six questions and maybe you can stave off some drama, heartache, and friendship loss:

  • If we weren’t friends, would I consider her compatible with me as a girlfriend? Does she meet my criteria?
  • Does she engage in any of my deal breakers?
  • Has she dated other friends? How did that turn out?
  • How does she talk about her exes? (this doesn’t matter so much as friends and may even be a bonding point, but it really matters as a girlfriend and can reveal red flags)
  • Have we talked openly about dating? What has come up?

This takes the situation from being unconscious and unaware to intentional and adult-like. If this can’t happen, then chances are the relationship won’t be intentional and adult-like.

  • WHY do you want to date?

Is it loneliness? Is it because you think you can’t find someone else? Is it because you’ve always had a sort of crush and now you’re both single? For me, I learned that if the answer is “why not date?”, it’s best not to go there and stay just friends.

As long as our community remains small and rather tight knit, it’s likely that we’ll run into the same women in our dating adventures again and again, even within our friends group. When given the chance to date a friend again, I would pass, given my previous disastrous outcomes. Maybe the key question to ask, above all others is really, “Is it worth the risk?” Because, let’s face it, when it comes to love, sometimes you just have to leap.