AdviceChoose Your CityColumnsNew YorkSan Francisco

Ask A Grown Up: Ex Sex And How To Avoid Dating Assholes

The Bay's best newsletter for underground events & news

Good afternoon, Broke-Asses! So, here’s something personal about me: I’m married. To an awesome guy who loves me and treats me well and encourages me to follow my dreams. His name is Paul. He is British (ie: sexy as fuck) and my very favorite person in the world, besides my mother.

I am very lucky. However, it took me until I was 39 years old to find my awesome life partner, Paul. Before that, I dated a copious amount of assholes. The majority of the assholes I dated were in San Francisco, but there were quite a few here in Chicago, too. Examples of what I put up with prior to marriage include:

  • Let’s start with the guy who invited his best friends along with us on our first (and, only) date (a couple who spent the entire evening drinking and fighting, to the point that the maitre d at the House of Prime Rib asked them to leave) and who subsequently spilled two glasses of red wine into my lap.
  • Then there was “Guitar Hero,” who got  his moniker due to his desire to play video games, rather than have sex with the naked girl he’d invited into his bed.
  • And, the recently divorced dad of two whose ex stalked us on our dates – including the afternoon we went to Napa for wine tasting. (BTW – they’re back together now.)
  • The Longshoreman, age 35, lived at home with his parents and after our first date started calling me at obnoxious hours of the early morning (like, 3am), asking to come crash in my bed because he’d been out with his buddies doing blow and drinking and he couldn’t go home in that state to his mommy.
  • And, lastly, the PhD student who was wayyyyy into public sex and tried to convince me to give him a hand job under the table at dinner… on our first date… within an hour of meeting.

I am very lucky. I hated dating and am so fucking glad that I don’t have to do it anymore. But, you know what all these miscreants of romance had in common?


I was the common denominator in all these bad dates.


This date is not going well. It’s totally the vest.

This week’s question comes to us from C.K. who asks:

“How can I avoid ending up with an asshole like my ex-husband again?”

Oh, C.K. – I wish I had some magic formula to offer you that would prevent you ever being subjected to another toxic relationship like the one with your “ex-hole.” Unfortunately, and to the opposite of what eHarmony’s founder claims, dating is not a science. So many things have to be right in order to create a healthy, sustainable relationship.

The primary being your own head.

My mom (who is very smart) told me something when I was very young that it took me until I was an adult in my 30s to believe:  Desperation attracts desperation and emotionally damaged people do not attract healthy people. It is when you are not focused on finding love that you actually find it. And, nice guys/girls/other are the best partners.

Really, the best way you can avoid ending up in a toxic relationship like the one you just ended is to take all the time you need to ensure that you are over it and you are in a good place where you are happy, fulfilled and content with your own independence before you start dating again.

Because, as much as your ex is an asshole, you were also a part of that relationship. Whatever was going on with you contributed to the toxicity of your marriage. Even if it was subconscious or unintended — something pulled you to someone who was incompatible and kept you engaged with him. You have to figure out what that was and fix it before you can avoid making the same relationship choices as you made prior.

The common denominator is you, right?


After your soul searching self discovery, (which will suck, sadly) there are a few things you can do to narrow the chances of ending up with someone who is  completely incompatible for you and treats you badly:

  • Decide what characteristics are important in whomever you date: Kindness, hard working, family oriented, sense of humor, etc… If the person you are on a date with lacks any of those key qualities, consider that a red flag and take a pass on seeing them again.
  • Know what you want and don’t settle for less. Divorce is hard and can make you feel like you are less than. But, I’m here to tell you that isn’t true. You are awesome, you are all that and a bag of chips! You deserve happiness and a fulfilling relationship. If you aren’t getting what you need from someone you are dating, reassess the relationship and don’t be afraid to just end it.
  • Be happy by yourself: You know what did it for me, C.K.? I met Paul, the wonderful man that he is, when I had finally just said “fuck it, enough is enough” and stopped dating because I was happier by myself than with any of the idiots I had been going out with. In fact, I had sworn off dating (as I’d been dating a loser off and on for six months) and when Paul asked me out on a date. I told him that we could go out “as friends” and nothing more. And, the rest just happened because I wasn’t focusing on it or over thinking it or even considering it a date. If I had gone home by myself after our first meeting and never seen him again, I would have been just as content by myself as I was with him. Happiness breeds self-confidence and those are both very very attractive qualities which will pull in the right kind of person to build a sustainable relationship.
  • Lastly, know that good relationships are hard sometimes, too and require work: Anyone who thinks otherwise or is only interested in the “happily every after” fantasy of dating/marriage or isn’t willing to put in the effort is not worth a second of your time. Avoid these Peter Pans and fantasy land residents at all costs.

But, mostly, it begins and ends with you. If you are healthy and happy you will attract healthy and happy. If you know what you want and do not tolerate otherwise, you will magically grow a teflon coating that assholes like your ex will slide right off of… it begins with you. And, ends there, too. Good luck!

Got a question you need a grownup to answer? Email Kate at and your query might be used in a future column!

[Bad date image via]

[You’d still be an asshole image via]


Like this article? Make sure to sign up for our mailing list so you never miss a goddamn thing!
Previous post

MiFlight: Never Show Up to the Airport Hungover Again!

Next post

The Nine Lamest Things About Polyamory

Kate Rice - Supposed Grown Up

Kate Rice - Supposed Grown Up

Kate Rice is a freelance writer whose work has appeared on DollyMix (UK), BitchBuzz (UK), Broke Ass Stuart’s Goddamn Website, the Chicago RedEye, ChicagoNow, Wired: GeekMom, Bleeding Cool, Wizard World Digital, The Beat and GeekNation, where she also hosted the weekly podcast “ComixChix.” Kate has appeared on Good Morning America, WGN Radio and a slew of geek related podcasts. She writes the daily blog The Adorkable Grrl. Kate lives in LA with her #BritishHusband, her daughter, and dog Max. Follow her on Twitter @AdorkableGrrl or on Facebook or on Instagram @TheAdorkableGrrl