Ashley Kelsch Asks, ‘When Is It Okay for Friends to Date Your Ex?

The dating and relationship coach writes about communication, boundaries and knowing yourself

By Ashley Kelsch
Ashley Kelsch: Friends Dating Friends

Ashley Kelsch is Austin’s top certified, professional dating and relationship coach and former owner of Teddies for Betty’s, the lingerie boutique on 2nd Street that she ran for a decade. She offers one-on-one life-coaching programs to help clients acknowledge and understand limiting beliefs, to set boundaries and to learn how to change mindsets so they can get what they want in their romantic lives and feel empowered. Ashley helps men and women of all ages, single and married. She has a weekly podcast called Modern Renegadesand you can follow her on Instagram @AshleyMKelschRead more of her Tribeza columns here.

I remember this moment in time during my sophomore year of high school when my friend and I both noticed and fell for the same boy while standing in the lunch line. Each day, we hoped to be somewhere near or in the vicinity of said boy so we could maybe get his attention. At the very least, we wanted to be near him so we — okay, just me — could smell that intoxicating combo of his after gym sweat and Calvin Klein cologne.

This went on for weeks: My friend and I would stand there face to face, talking but not too seriously in case he wanted to speak with us. Or, we might stand side by side in silence so he knew we were there and available in case he wanted to say something … anything!

One day, as we were walking away with our foil-wrapped hotdogs or something, he said, “Hey.” We both turned and looked at him, and he added, “Would you like to go out with me?”

I started to answer “yes,” but didn’t get it out because my friend said, “Which one of us are you talking to?”

As fast and fleeting as that moment was, I do remember realizing that maybe he wasn’t talking to me.

Austinite and relationship coach Ashley Kelsch.

And then he looked at my friend and said, “You.”

I almost threw up in my mouth. My stomach definitely bottomed out and my face flushed thanks to a total disbelief along the lines of — “Wait, what? It’s not me you’re looking for?” The memory is almost visceral today.

That wasn’t the last time I’ve found myself in that peculiar space of being interested in the same person as a friend, or finding out a person I’m interested in has eyes on a friend of mine. It’s safe to say that I’ve experienced it more in adulthood than in high school. I’ve come to accept that dating in Austin (surely singles in any city or town can relate) is like being part of a very slow moving orgy. On some level, we are all connected.

I’ve come to accept that not always being the one the that gets picked is just part of dating. The pilates instructor and I may attract the same type of guy — or literally the same guy after guy after guy — or that my friends and I may drool over the same person.

What I find harder to handle emotionally (and I’ve heard from others who’ve experienced this as well) is when a friend, who knows the details of my dating history with someone, decides to go out with that person after me. You’re asking for a lot here if you think it’s okay to date from a friend’s romantic history.

Unless you have a conversation, that is.

Also, this doesn’t apply to any and all dates or persons. We are all adults and we get to do what and who we want. There may be potentials or partners in your past with no enduring emotional ties. Take him/her or leave him/her, it makes no difference to me. Others might remain sore subject matter, and it’s okay to be sensitive about love lost or the way a relationship unfolded when you cross paths or when a friend says their name in the context of their own dating life. For some, there is a grace period. For others, it’s non-negotiable.

Dating from friends’ history does raise questions that ought to be considered: What are my boundaries? Would I date a friend’s last boyfriend? What if they only went out a few times? Would I be okay with them dating people I’ve dated? Have my friends and I communicated about this stuff?

I’m not making anything up when I say I’ve been at a table with friends when everyone is swiping on and chatting to the same guys without knowing it at first. I’ve also met a friend’s new boyfriend who happens to be the last guy I was flirtatiously texting. Have you asked your close friends how you might handle that?

Would it be a fair request if a friend asked you not to date or sleep with someone he or she once dated? Doesn’t matter. It’s their boundary. That doesn’t mean you have to agree, but you might end up forfeiting the friendship. Will it be worth it?

My mom used to say, “Your friends will out burn the sparks that come in and out of your life.”

Maybe you want 100 percent loyalty from your friends in all circumstances, even if it means they might miss out on love. Maybe you have a friend who’s dated a ton of people and has unreasonable expectations about who’s significant and therefore off limits, so you take the request not to date someone with a grain of salt. Or you may be open to your friends hooking up with people you’ve dated — perhaps only after some time has passed. Most likely, it all depends on the friend, the former lover and how you feel about both relationships.

Being clear with yourself about what’s okay and not okay when it comes to friends and exes dating is required these days. I recommend thinking this through rationally before the situation arises and emotions take over. Communication is also key. Talk to your friends about boundaries. Don’t assume friends will know how you feel about these scenarios or a certain person in your past. You can’t expect your pals to be on the same page as you just because they swipe in the same direction as you.


Read More From the Outdoors Issue | Summer 2021


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