100 Emails, 20 Dates An SF girl's systematic quest to end her singlehood

Time for a check-in

When I started this blog, I figured I'd give the whole process a year. That seemed like a reasonable amount of time to go through the whole 100 emails, 20 dates conceit. I had no idea I'd still be doing this two years and a couple of months later. And quite frankly, now that I've realized it, it's hard not to be a little depressed.

But I also didn't consider how much learning I had to do. I mean, I'll be honest, I am terrible at this. Like really bad. And far worse than I thought I was. It took a good solid year or so to figure out how bad I was at this and to encourage myself to start at the beginning. Here are some of the key lessons I've learned:

1. Guys will take risks if they know the risk is worth taking. It's a woman's job to let guys they like know that they should take the risk. That's why women need to make eye contact with a guy an average of 13 times before they're likely to come over. If a woman doesn't flirt, how is the guy supposed to know he's not in the friend zone? Ladies, if you want a guy to ask for your number, you need to signal to him that you want to see him again, possibly by saying something cryptic like, "This was fun. We should hang out sometime."
2. If you're not in a relationship with the guy, he can't reject you. One of the great lessons of online dating is that you have to deal with "rejection" a lot. Guys flake on you. You flake on guys. They lose interest mysteriously. You lose interest mysteriously. It happens--a lot. If the guy never got to know you, he's not rejecting you because he never had the chance to get to know you. This is a really good thing to keep in mind as you try to cultivate the "NEXT!" mindset in your entire dating life.
3. I really hate online dating. I'm kind of an odd bird, so I make terrible first impressions. But if I meet a guy, and there's a spark, I can help fan that into a flame in person. Then, my follow-up emails are hilarious and awesome. But I'm terrible at starting with email. It's like a doubly bad first impression for me. And then, it's so much work just to meet someone. And my age gives me an unfair disadvantage because guys date younger. It's demoralizing. But I'm giving it one last shot.
4. If you're single, you need to figure out what makes you hot, then work it. Everyone has something about them they should flaunt. If you don't, work on your arms. Those are fairly easy to turn into a hot little gun show. Calves, too. When I figured it out, it helped me dress more flatteringly (ex.: straight skirts, not full skirts). Knowing that at least one part of me was sexy helped me feel sexy all over. Also, Pilates helps.
5. Trust your gut. I think I'm terribly at reading signals, but I'm really not. I just believe that I'm not. When I look back on mistakes that I've made, I know that I knew what was going on. I just didn't want to admit it. I don't fool myself nearly as often anymore.
6. More girls (meaning me) should take a more "guy" approach to dating. No, male readers, I don't mean that girls should sleep with you on the first date. I mean that for many guys, happiness is the absence of unhappiness. For many women, unhappiness can sometimes be the absence of happiness. There's an emotional zone halfway or so between happiness and unhappiness where guys are still happy but women are kind of meh. I need to stop thinking of meh as a negative, and if I feel meh about a guy, I should focus on the positive and give him another chance.
7. Courage. It's not just Dan Rather's temporary and poorly chosen sign-off, it's also a good dating mantra: nothing ventured, nothing gained. Often, in dating, you just need to take a (calculated) risk or else you won't get anywhere.
8. There are a lot of really cool, interesting, and nice guys in San Francisco. I always knew how awesome my bros and other guy friends are, but reading back through my posts, it really struck me how many nice guys I've met over the past two plus years. I'm pretty fortunate.

I'm sure there are more, but this is a start, at least. Onward and upward.

Email 19, Date 6: For real this time, I shouldn't date an engineer

Even though I had completely given up on dating in a fit of extreme frustration, I kept my OKCupid profile up. I didn't check it, I didn't even get on the site, but I figured, if someone saw it and felt inspired to email me....

N. apparently did, and he responded to my "The most private thing I'm willing to admit here" section of my profile: I have a deep, abiding affection for classic country and honky-tonk (Johnny Cash, Loretta Lynn, George Strait) -- but I don’t expect you to share my love of music that relies so heavily on tortured metaphors, melodramatic vocals, and awesomely twangy guitars.

Date: 7/14/09
Subject: Hiya

Well, it's the usual story, I guess: your "profile photo" caught my eye, your other photos held my attention pretty strongly, and what you wrote about yourself sounds great, too (yeah, I do eventually get beyond the pictures). I'm definitely a collection of opposites, too, esp., now that I think about it, the ones you mention. I like your style and attitude, too, *and* you're pretty damn cute!

For what it's worth, amongst my music choices I've got a decent little collection of country music. I've got, in alphabetical order: The Carter Family, J.Cash, P.Cline, S.Earle, Lyman Enloe, Wanda Jackson [sort of counts?], Little Feat [ditto], L.Skynyrd [ditto again], T.Wynett, as well as stuff like Lucinda Williams, John Prine, Pete Droge,.... I say "hurray" for tortured metaphors! (Just not all-day/everyday, like anything else...)

So here I am. I'm intrigued -- write back if you are, too.

I was intrigued. I had seen his profile before. I may have even emailed him before. In one of his photos he was really hot: slightly chiseled features, eyes that sparkled with life, and attractively nerdy glasses. In his two other photos he was... Well, he looked 47. His age was the only reason I could think of that I hadn't emailed him. But at 47, he's young for the guys who are drawn to me online. So I, with absolutely nothing to lose, wrote a ridiculous email back, riffing on the following items:

• He wrote me on Bastille Day.
• He included a link to a Belgian website in his profile.
• Belgians and French have a rivalry.
• He admitted in his profile that he doesn't want to date people who live outside of SF.
• I genuinely admired his honesty about that, while admitting that admitting to that made me feel shallow.
• He described himself as quirky and brainy in his profile.

In his next email, he suggested we meet for a drink. In mine, I admitted that my only night free was about five days later (tonight). We made plans, exchanged a few more emails, and met up.

One could describe my attitude toward this date as pessimistic but open. One could also describe it as petulantly reluctant. In reality, it started off as the latter, then when I realized it would be cowardly to cancel, it became the former.

We didn't click. At all. But when he said that he was an engineer, that clicked.

I have nothing against engineers--two of my bros (who I love dearly) work as software engineers--but I can't date people who are engineers. My dad was an engineer. Two of my ex-boyfriends were engineers--no, actually, three. It's a way of thinking, of viewing the world as problems with single, definite solutions, that does not work well with my world-view that things are complex, that there are usually multiple good solutions, that not everything needs to be fixed. And perhaps most importantly, that I am not a problem that needs to be "fixed."

As I observed how N. took in information and processed it through an engineering mindset, I kept thinking, "This is excruciating."

To be fair, the conversation was not anywhere near excruciating. He was a really nice guy who had done a lot of really interesting things in his life. What is excruciating is that I know that I can't be with an engineer. I've learned that lesson. And yet I keep attracting them. And in times like this, when I am in desperate need of an ego boost, I entertain the thought of dating them.

So the next phase in 100 Emails, 20 Dates will be identifying things like this: patterns that have gotten me to where I am today--36 and single with zero prospects. The next phase will be fixing those problems. Expect many bumps in the road.