Austin Dating Coach Ashley Kelsch on Protecting Your Past

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 Renegades, and you can follow her on Instagram @AshleyMKelsch.

When I was in my mid-thirties, I was on a date with someone I’d been out with several times over the years when I had an encounter that I’ve never forgotten. We decided to stop by Arlyn Studios for an afterhours South By event to say hi to friends and check out bands that were playing. It was crowded – and like most events in Austin, packed with familiar faces.

On our way into the venue, we passed a man heading out the door. He and my date casually greeted each other with a “Hey man, what’s up? Good to see you” fly-by. I remember looking at the man and saying, “Hi, nice to see you,” while simultaneously thinking, “He looks familiar, but how do I know him?”

Before I could piece it together, my date turned around and said, “Did you have sex with that guy?” We had barely made it through the door. I froze. Then I laughed awkwardly and said, “Who was that? He looks familiar but I can’t place him.”

The guy I was with then gave me his 1-star review of the man who’d just left while I stood there not really listening nor interested in figuring out how I knew the guy but in disbelief that my date asked me something so directly that was so personal.

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When he finished, I looked at him and told him that who I have had sex with isn’t really his business unless I choose to make it so. In the future, I added, please don’t ask me that again.

It occurred to me that I had never advocated for myself in this way, which explained my hesitation and my delayed response. I remember thinking, “I’m damned if I do and damned if I don’t.”

Earlier in my dating life, which started in my 30s, I thought I was supposed to share my dating history with new men – especially if we were in the social settings with someone I’d been involved with. I believed it might be weird if I didn’t mention it and they found out later.

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But buried in that belief was me doing something I wasn’t okay with for the sake of the other person. I didn’t want him to feel uncomfortable even though protecting him would make me feel uncomfortable.

The catch was that sharing my dating history didn’t usually go over well. It turns out some guys – even though they ask – don’t want to know about my intimate life. So, what I thought might be useful information didn’t serve either of us. In fact, these might have been some of the most awkward dating moments I’ve ever had.

Now, my past is my business unless I chose to make it yours, which will likely happen if we get close and build trust and feel safe together.

There are some gray areas to be considered in a city like Austin. Despite having a population of almost a million, it can still feel very much like a relatively small town when it comes to dating. Maybe you’ve heard it referred to as “the slowest moving orgy?” Maybe not. But now you know.

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The point is: it’s not uncommon for a friend to connect with someone on a dating app that you’ve dated or know. When they tell you about their new potential love interest, you might want to let them know your history with that person.

Maybe your friend would be mortified to have sex with someone you’ve been with. Or maybe you have relevant information about dating that person. This happened with one of my friends. So as a courtesy, if she asks, I’ll tell.

Or maybe you ask – or tell – because the person you’re early dating has boundaries about dating friends’ exes or people his buddies have been intimate with.

Information like this should be shared in the spirit of respect and honesty. In my opinion, it’s fair because it’s not coming from a place of jealousy or because someone feels threatened. But this business of being out and about, running into people and just asking personal questions is not cool.

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According to a poll on my Instagram, 86 percent of you agree.

Most of you said, “We’ve all had sex with other people. No need to share.” Some thought it was a “red flag” for someone to even ask, while others felt that their intimate lives are sacred and shouldn’t be discussed with those who aren’t involved.

To the other 14 percent who want to know all about a lover or potential lover’s past, I would ask you to consider why you want to know and to be honest with yourself about that. How is knowing this going to serve me and my date?

I also believe that sharing and divulging this type of information isn’t necessarily fair to the other people involved. I’ve become much more private about my intimate life in the years that have passed since the incident at Arlyn Studios. I don’t share details with friends the way I once did. And so now I think that maybe, just maybe, the other person involved might want the same privacy – or at least a say in what is being shared about his or her personal life and history.

It’s not just my dating and sex life, but theirs too. This doesn’t come from a place of secrecy or shame either. I’m okay with my past, who I’ve shared time with and how. That’s the truth.

Just remember: If you ask about someone’s past, you’re the one who will have to live with the information and what you let it mean.

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