30 Dates in 30 Days

About 7 years ago one of my friends dared me to go on 30 dates in 30 days. I didn’t originally agree to the dare. I really hadn’t dated in the true sense of going out on dates. I was scared. I had spent the last 10 years in a relationship; 8 actually being in the relationship and 2 getting over it. I agreed to the dare because I really believed that if I was going to start dating again, then this would be the way to do it. This was like diving into the deep end of the pool and I am not the “dip a toe in” kind of girl.

I knew that in order to be able to stack the odds in my favor that I actually could rack up enough guys to participate in this, there was only one option… craigslist. I was a newbie to dating, so I had limited perspective. I began looking at the Men seeking Women. I remember reading the posts and being totally freaked out. Who were these guys that posted? What does this guy even look like? And how do I respond?. “Hi, I’m a 30 year old bay area native who likes to hike and do yoga.” I had no idea what I was looking for or really how to describe myself. I started to hate the idea of “selling” myself.

Then I read the women seeking men posts. I was more freaked. I was snarky as I read post after post of women seeking their prince. Except these princes drove a BMW, worked in finance, and were ready to procreate immediately. I was more scared now. I wasn’t one of them, but at the same time I was. We shared at least one thing in common: we wanted a date. So I began to craft the profile. I remember it simply said, “I just want to meet for a drink. You’ll let me beat you at pool even though I am the worst player ever and know what whiskey to order. You know a dive from a hotspot. You are the kind of guy who is known for being funny, the drier the better.” And then I included some basic facts about me, the age, location kind of stuff. Then I clicked “Post”.

The next morning I was overwhelmed. I had to go through all these responses. I think the first group I eliminated was the “dirty bird” group. These were the guys who sent the nude pics or outrageous descriptions of what they were going to do to me. I think my favorite of the bunch was the picture of the cowboy in chaps and nothing else. Next to go were the guys who sent what I termed the “form responses”. You knew, just like the dirty birds, the form response guys didn’t read anything you wrote and probably copy pasted the same reply to ever women seeking men post on craigslist. I figured if they didn’t bother reading the post, then drinks would probably not be very fun. I would end up listening to some stranger talk about himself endlessly until I could finally figure out some way to end the evening. And I think last to go were the guys I deemed age/location incompatible.

Of course, I also viewed this as an opportunity to meet all kinds of men. My selection ran the gamut from computer tech types to surgeons to carpenters to students and even one bounty hunter. Actually it turned out he wasn’t really a bounty hunter. He had been on disability for 5 years and I didn’t get to hear any good bounty hunting stories, which was very disappointing. But I digress.

30 dates in 30 days was exhausting. There were days I had to book morning and evening shifts, due to scheduling. There were the countless nights of staying out too late. And then even the dates that ended early still included giggling with girlfriends over the phone talking about it. The worst date ended with me climbing out a bathroom window of a dive bar and the best included a couple friends I still have. Not much has changed since I posted back then. I still drink whiskey, I still love a great dive, and I still am terrible at pool. I think the only thing that has changed is my selection process.