Starting to Date… at 30

So I decided when I turned 30 that I needed to be serious about dating. I had a few serious relationships, but I decided it was time I stopped focusing on my career and start focusing on all the other things in life. I’d lived in Portland 12 years (the longest of anywhere I had been) and consider it my home, so why not start looking in the fair city I love? Did I miss the boat? Was I supposed to be focusing on getting married in my twenties and I blew it my focusing on education and career first? Damn.

I am successful, financially stable, and gosh darn it people like me. So with a heartfelt vow to become serious about dating I decided to dedicate myself to finding love.

I’m a nerd, total and complete geek. So whenever I am going to try something new, I research the hell out of it. I decided I needed a new approach to finding love. I can’t just wait for someone to fall into my lap! My college days were over, and thus were the chances of anyone falling into my lap. My career isn’t the kind you date coworkers. So I needed to figure out, at 30, how the hell you do this thing called dating.

This over-researching thing is a hallmark of my personality. It helps and sometimes… damn. Anyone who has spent too much time on WebMD may have an idea of the kinda trouble a person can get into.

I started reading all sorts of – ahem- I’ll loosely call this “literature”; The Game, Modern Romance, The Rules, Me Before We, Cinderella Complex, Ho Tactics

I watched hours and hours of YouTube dating coaches. Matthew Hussey, Amy Young (who I actually really like), TED talks on how to “hack” dating…

I stalked Facebook. Oh yes. “For research”. How did my married friends do it? What about people struggling to find dates? What was the secret?

I spent time reading books on how to talk to people, dating for the shy, and how to fake confidence… I am a bit socially anxious, but it comes out as seeming outgoing (I laugh a lot and smile nervously). However, I was terrified of actually dating. I had 3 serious relationships at this point, my high school boyfriend, a college boyfriend and a coworker. Serial monogamy and not much chance to actually DATE.

Everyone I talked to about my research said practically the same thing, “I can’t imagine dating in my 30s. I wouldn’t even know what to do!”

Yeah, I wasn’t finding much in the way of answers either.The research I did was confusing but could be boiled down to the basic advice of “be attractively aloof [insert gender here] likes a little mystery”. Seriously, dating and pickup books for men AND women basically say the same thing. Try to get the other person talking, don’t talk more than them. Don’t be overly responsive or available because it seems desperate. Don’t be clingy. Each of them had a million silly rules or pieces of overly-prescriptive advice that were all intended to give that impression. The Game and The Rules might as well have been written by the same people. There. I just saved you MONTHS of your time.

It wasn’t all the same old stuff though, people like Amy Young really emphasized personal growth and learning to be happy as a person without needing to be completed in a relationship. About getting over difficult feelings and understanding your reactions. I think they may have had the most impact on my willingness to actually date.

So… armed with “research” I decided to go full force with my plan to find an avocado. I would go to Meetups for Singles, date online, and I even booked a ticket for speed dating. When I decide to do something, I go all in.

Everyone knows that a plan never survives first encounter. What in contained in this blog are the collected stories of trying to find love in the City of Roses. Detailed embarrassment, rejection, nervous successes and mostly hilarious.

Do YOU have a story? Please send it to me at and I’ll post your story anonymously (or with credit, if you want!).



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