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

6Apr/094

My new favorite dating site: Crazy Blind Date

I had a bit of a dating-related freak-out a week or so ago. I was spending so much time at my computer, looking at profiles, sending emails, checking my email, and it all felt like such wasted effort. At the same time, I felt trapped in my house, that life was kind of passing me by. I've never been the kind of person who waits until she has a boyfriend to do X, yet suddenly I felt like my entire life was on hold until this search was over. But how was I going to find someone when nothing I was doing was getting me anywhere.

So I thought, I should go gonzo. Sonia suggested speed dating (I'm still looking into that), and my friend K. emailed me with two brilliant ideas.

  1. Quiz dates. Team pub trivia for singles.
  2. Crazy Blind Date. Spontaneous blind-dating.

K. totally took the lead on the Crazy Blind Date. She signed up, went on a date with someone the next night, and had a great time. She said there wasn't really a love connection, but they both said they'd like to hang out again.

So inspired by her speedy action (and speedy results), I signed up. I filled out the basic information (it's really minimal), listed what days I was free, what neighborhoods I could meet someone, and how much notice I needed before. I listed four times I was free and got fixed up on two dates.

About a day before the first one, I got an email from CBD saying that they found me a date. I was supposed to meet L., 32, at a particular time and a particular neighborhood. I got to choose the place from a list. They also gave me a few details about him such as "Things I'm good at talking about" and "What I expect of a date." In other words, really just the bare minimum you need to start talking to someone. Except--no picture. You see a highly pixellated picture, and you can see how they finish this sentence "You'll know me because I look like..."

A half hour before the date, CBD sends you a text to let you know that they've opened up a relay between you and your date, so you can text each other through CBD without revealing your phone number. It's perfect for "I'm wearing a red shirt and jeans" or "I'm sitting at the bar, green pants."

Then I got there. I quickly found L. and ordered myself a beer, then we grabbed a table. I was amazed at how easy it was to have a real conversation. The job stuff came up, of course, but since you know so little about the person, you just dive right into really talking. It was really, really fun.

L. and I got along great, although I don't know that there were any sparks (he did have a rad Scottish accent and, as faithful 100E/20D readers know, I have a thing for voices), but we talked about hanging out after he gets back from a work trip (coincidentally, to this Swedish town I have been dying to visit).

After the date, you fill out a brief feedback form: Did the person show up, how would you rate their attractiveness, how would you rate them as a date, etc. Through that, you can also send them a message and allow (or not) CBD to give them your phone number and email address.

I also went on a CBD on Sunday with J., who coincidentally went on a date with K. on Saturday. She's been on four CBDs so far, and has had really good, fun experiences with all but one. (They ask you to stay at least 20 minutes. She couldn't get out of the conversation, so she ended up staying for an hour before she was able to make her exit.)

Here's what I love about it:

  • There are zero expectations, so you can let the conversation be what it is.
  • It gets me out of my house and meeting people right away.
  • I get to try new bars.
  • It's by the same people as OKCupid, and it's got that same "Dating is fun! Meeting people is fun!" attitude. I love that. It should be fun.

I just canceled my Match subscription, and I think that, for now at least, I'm going to focus on OKCupid and Crazy Blind Date for online dating.

The only question is, what do I call these in my accounting? It doesn't seem right to count them as dates.

26Mar/090

Is age discrimination in dating wrong?

My coworker A. and I were talking the other day about how frustrating it is that guys in San Francisco seem to be in this state of arrested development. They can have kids whenever they want, and when they decide that's what they want, they can always date someone younger. So, they get a free pass until...mid-30s? 40s? 50s? After dating guys her own age who just wouldn't deal with their lives, she's dating someone about eight years older. "He's a man," she said. He plans things, he takes responsibility, he's got his act together. Yay for A.!

A. said that her guy friends started to feel the urge to get serious around age 33. My friend R.'s roommate said something similar. When he was younger, he said that even if he was with the right girl, he wouldn't marry her. Now, at age 33, he feels that if he meets a good girl, he has to marry her because he's running out of time. A's friends don't seem to hear any clocks ticking. They prefer not to date girls in their mid-30s because women at that age could be in a rush to get married, and they don't want to be rushed.

I do suspect that this is one reason why I don't get more responses on Match. At 35, I'm at the age where some guys think I want to get married right away. They don't want the pressure, so they don't write back. I understand, but it feels deeply unfair. I'm a good person. I'm smart. I'm cool. I'm in a band, for god's sakes! I do want to get married and have kids, but not immediately.

Years ago, my now 41-year-old brother said that he wanted to be like our dad: he wanted to marry a hot, younger chick. And, oddly enough, a few years ago, he fell in love with a hot, younger chick who's perfect for him, and he's marrying her next year. She's my age.

I don't want to be like our parents. My dad was almost 50 when they had me (my mom was almost 40), and there is a serious generation gap between us. That's one reason why it's frustrating to me that so many of the guys contacting me are significantly older. I was talking about this to Sterling, of the Bros Roundtable, and he said, "To be fair, aren't you doing exactly what you're accusing guys of? You're ruling these guys out because they're too old."

He's right, of course. But why is it so damn hard to date someone my own age?

24Mar/094

What the hell am I doing?

I've been seriously questioning the value of all this online dating nonsense. It's a lot of work, a lot of money (in the case of Match), and I've met only one nice guy through it (not through Match -- I'll post about him later). In the meantime, I'm spending all this time at home, alone, on my computer, trying desperately to get return emails. In the meantime, I'm missing out on all these things that I want to be doing.

Online dating sites are kind of like virtual bars, right? Match is like the big, pleasant bar with the obvious neon sign. Everyone goes there first. If they like the people there, they stay and they hang out. If they don't, they just end up being virtual wallflowers, sipping their beers, and trying (perhaps in vain) to talk to people. It works for a lot of people. Two of my friends met their husbands through Match.

I think what I'm realizing is that Match isn't really for me. It's so much work, and for me, there's no payoff. I've only met up with one guy from Match, and as you can all see from my ever-increasing tally of emails sent, it's not really from lack of trying. Yes, I could try harder. Of course I could. But I still don't think it's quite the right place for me.

People there are all about what they do. I'm not really about what I do. I mean, I play music, but I don't want to talk about music all the time. I like traveling, but it's more about the little experiences, eating an eclair by a Japanese patissier on a sunny day in Jardin du Luxembourg. I don't care about crossing off countries as if they're on a big to-go list. I like having smart conversations and doing stupid things and struggling with the crossword on a Sunday morning while eating a big, gigantic homemade breakfast. I want a home that feels cozy and welcoming, where friends drop by and we have big BBQs in summer and game nights the rest of the year. That doesn't really translate on Match. Or at least, I haven't been able to make it translate.

I need a new strategy. I need to actually meet people, like in the real world. I'm open to suggestions, people. I don't need cheerleading, I need strategy. In the meantime, I'll do a third revision of my profile and see what that gets me.

24Mar/092

Email 14: Smiley faces are not endearing

I'm 35. I'm beyond the age of smiley faces. Yet, I can see their purpose in email, text, IM, etc., when you don't have any body language or tone of voice to get your cues from. Sarcasm, for example, can just come across as bitchy if you don't follow it up with a :) or ;).

This guy's profile was chock-full of :O) smiley faces. I thought, maybe he's just trying to be cute or doesn't quite know what to say. He did have some thoughtful things, too, like how at our age, you just have to accept that everyone has baggage. It's the scars of living a life. That's maybe more eloquent than he put it. He's also a musician (plus) and lives on the peninsula (minus, but not dealbreaker). I wrote him.

Subject: Everyone does have baggage
Date: March 5

I loved the line in your profile about everyone having baggage and that it's silly to deny it. I had a friend once who, in college, said she never wanted to date any guys who hadn't been crushed (her word) because there's something valuable that you learn from that experience. And by the time you get to be an adult, it seems that if you haven't been hurt, you're either freakishly lucky or you just haven't been trying to find your person.

What's the cover band? A friend of mine and I used to dream about starting a cover band together. I envy people who know that many songs. (It's easy in bluegrass -- you only have three, sometimes four chords).

He wrote back about an hour later.

Date: March 5

I don't know what else to say except.... YUP! ;o)

Seriously, it was really kind and sweet of you to acknowledge what I had to say about the subject. I mean come on, puh-LEEEEEAZE! Right? And I HATE that we've all had to have been "crushed" to become this way, but I guess it is just "due process" at this point... Yeah, I think we ALL would've liked to have found the loves of our lives the first time out, but then you KNOW that most people who've done that might have been wondering, "Hmmm... Maybe I settled or should've found out a little MORE about myself first, huh?" I don't know... Just another "perspective" on the whole thing, I guess?! Oy...

The cover band would be [Funny name of band]. LOL! And when I think about it, yeah it is pretty staggering how many damn songs I've learned/played over the years?! Good to know I put the old noggin' to good use for SOMETHING, right?! Again, oy... LOL!

And I think it's WONDERFUL that you play Mandolin... I've always been kinda terrified of it with it's skinny little neck and different tuning and all... Hee!

Alrighty then... Enough of my ramblings for now... Thanks for "stalking" (as they call it here) for profile! Yours is wonderful, by the way... *Blush*

Ummmmmm. I didn't write back. He IM'd me on OKCupid a couple of days later.

Hey there... I'm assuming you got my reply to your note?

Whoops... Maybe you're away from the computer, oh well! Just wanted to say "hi"... Hope you have a wonderful day! I'm gettin' outside myself while the weather's so nice... See ya!

And then he emailed me again. With the ;0) smiley face. I know it sounds really lame to not be interested in a guy because of smiley faces, and let's be honest, that's not the reason why. There's just something about his energy that is really, really turning me off. I found his email exhausting to read. And the smiley faces are part of that.

24Mar/090

Email 16: The traveler

As my friend R. pointed out, everyone on Match loves traveling. This guy talked about how he loved traveling, but his job (in something science-related) was preventing him from traveling more. He also loves listening and creating music and wanted someone who shared his values. I listen to and create music! I have values!

He never wrote back. Maybe he was traveling?

Subject: Bitten by the travel bug
Date: Mar 6

Hi!

Sometimes it feels like torture to have all these amazing places to go in the world, and the ability to get there and experience the phenomenal things they have to offer, and yet not have the time. I work on a brand-new travel magazine, and while we're getting it off the ground, we have pretty limited vacation. So all day I'm working on stories about the campesino food "renaissance" in Mexico or tango shoes from Argentina (for our product section -- they're engineered to make it easier for women to walk backward!) or quirky theme cafes in Tokyo and trying to narrow it all down to figure out where I'm actually going to go with my one week that isn't already spoken for. (I'm thinking Croatia -- both to Istria to research a confusing twist in my family history and also to see the Dalmatian Coast.)

So if you had a month off to travel (or six months, while we're talking hypothetically), where would you go?

24Mar/090

Email 15: Cyclist number two

It's attractive when guys, or anyone, really, knows what they want. It's even more appealing when they seem to be describing you. This guy was looking for an artsy, creative, athletic, spiritually conscious, fun-loving type. That's me! Well, I'm semi-athletic. I do athletic things. And he's a cyclist. I must have been on a cycling fix or something. He also talked a lot about being up for anything, having an adventurous spirit, and taking risks.

Subject: Pro-fixie or anti-fixie?
Date: Mar 4
Hi!

I was just looking at your photos and saw the one of the "One less fixie" sticker on the bike. Are you pro-fixie or con? A friend of mine explained to me that he started riding a fixie to work to build up his leg strength for a triathlon he was training for. This still didn't help me understand the appeal, since I always went for consistent RPMs (I'm still working on that, though).

I love that you're looking for someone with an "I'll try it" attitude. I've learned that I work best with people who say "yes" (or at least "sure") more than "no."

So what's the best risk you've ever taken?

He wrote back not long after.

Subject: Pro-fixie or anti-fixie?
Date: Mar 4

Hi,

I'm off and running for work so I'll have to think about my "best risk" and get back to you later today.

Thanks for the email, I loved your "cat people vs dog people" analogy... it sounds like the roots to a good bluegrass song...

I'll write again soon, cheers-

He didn't write again soon. And then I thought, do I write him back? He said he'd write me... I didn't write him back. Maybe I'll message him again. Maybe I won't. He did have something about sexual compatibility in his profile, which, sure, if it's important to you, maybe it makes sense to put it in there, but it also sort of feels like putting the cart before the horse.

24Mar/090

Email 13: Life observations

One of the reasons I really love Twitter is that I can share the little daily observations I make with my friends--all those things that make you want to turn to the person next to you and say, "Did you see that?" Like the black Lab in my neighborhood one time holding a stuffed mallard duck in his mouth, as if he had just retrieved it from a hunt.

This guy's profile started off with several sweet observations that he'd made recently. He said he was attuned to people and their interactions. He's also a cyclist and likes hosting game nights. Win! I emailed him a couple of weeks ago, in one of my "I'm going to email one guy every day" phases.

Hi--

I love those moments when you feel like you deeply observe what's going on around you. I remember one time, when I lived in Portland (in a poor neighborhood) seeing a woman get on the bus with her barely-toddler son. The way they interacted reminded me of the Madonna and child -- a living pieta. Those moments can really stay with you.

I'm fascinated about your job. Tell me more! After I did a triathlon in 2004 (I've switched to the occasional half-marathon since then), I got really into cycling, then the Tour de France, then the physiology of Lance Armstrong (my theory is that he's clean but superhuman) and how someone's body type sets them up for success or failure in a sport. Maybe it's just me projecting -- it wasn't until I realized I had bad depth perception and just focused on running, etc., that I realized I could be an athlete. It was such a turning point for me.

So what board games do you play? Game nights are the best.

Nada.

Next!

14Mar/090

Everyone does like music

After my conversation with R. (and three of our three married or engaged friends) about how everyone's profiles on Match say the same things, I saw this online profile word cloud from Matt on the Plenty of Fish blog.

Women's interests word cloud

Women's Interests in Plenty of Fish Online Profiles

Men's interests word cloud

Men's Interests in Plenty of Fish Online Profiles

Matt analyzes it a bit, and while the results aren't entirely suprising (women's listed interests indicate bonds, men's interests are more activity-based), I always find it fascinating how that comes through in something like the interests section of an online dating profile. He did find some gems, though, such as that men list cooking more than women.

9Mar/093

Email 12, Date 3: The "resume date"

For some reason, the only people I get matched up with on Match are in their 40s. So when J. (45, musician, blah blah) emailed me, I thought, "What the heck? Maybe I should be open to guys 10 years older than me."

Date: March 1
Subj: Musicians are the best...

I enjoyed reading your profile. I think we have at least one very special thing in common, which is hard to find in a mate, music. I have a business career, but still make music a big part of my life. I've been playing in bands for a very long time, and still do.

Please have a look at my profile, and if you think we should learn more about each other, let me know. I'd love to come and see your band some time.

Happy Sunday.

I have a (minor) quibble with the "we have one special thing in common which is hard to find in a mate" thing. My friend R. and I were just talking about this on Sunday. She said, "I don't think everyone loves traveling the way that I love traveling." I said, "It's the same with music." Everyone on Match is into traveling, hiking, music, and trying new restaurants. (Our friend Annie had a friend who didn't like traveling or hiking, and she quit it because she couldn't find anyone.) It's not that special.

Anyway, I wrote back.

Date: March 4
Subj: Re: Musicians are the best...

Oh, I bet you say that to all the musicians.

It's so great to have that balance that you mentioned. I worked for a while (six years, actually) at a guitar magazine. It was my absolute dream job when I started -- and again when I got to head up the relaunch of our magazine for beginning players -- but after six years, music felt like work. Thankfully, a new job, playing some different styles of music, and a little bit of time helped me find my love for playing again.

So what kind of music do you play? What's your favorite thing to do in the Virgin Islands? (I've never been.)

His response:

Date: March 4
Subj: Musicians are the best...

I have a friend that works at a guitar magazine. His name is [redacted]. Maybe you know him?

I play a few styles of music, but mainly rock, classic rock, funk, pop, r&b, country, blues, a bit of swing. Been in many bands, done a lot of road work with national acts. What about you, what kinds of music do you play?

Favorite thing in the Virgin Islands is BEING THERE. Nothing like it. Most beautiful place on earth. But, to be more specific, I have chartered sailboats down there many times, and also done a lot of diving, snorkeling, and hiking. And eating and drinking, of course. :)

Want to talk on the phone? See if we hit it off? You can reach me at [redacted]. If you'd rather keep writing, write away.

Good night.

I told him I'm terrible over the phone (I am), but that I'd be happy to meet him for coffee. We made plans for Saturday afternoon, and I started to pick up a little type-A vibe as we settled on a place.

Saturday afternoon came, and I really didn't want to go. I don't want to date someone 10 years older. My dad is 10 years older than my mom. I don't want that. I was totally dragging my heels, but I thought that, at the least, it would be good practice.

I was running late, but Muni arrived in perfect time, and I got off the train -- two blocks away from where we were meeting -- at 1:53. Perfect! As I'm walking up, my cell starts ringing. It's J., wondering where I am. I know that people's clocks can be set differently, but come on! Give a girl a five-minute grace period before you call.

The place was packed, so we went to a nearby cafe and sat at a sunny spot near the window. The sun was shining in my eyes, which I didn't entirely mind, but I had that squinty, half-smile, sun-is-directly-in-my-face expression.

We didn't really have anything in common (except that we both play two different instruments in very different styles), but he proceeded to launch into what I like to call "the resume date." He listed off his work accomplishments, his musical accomplishments, the places he's been on vacation. How he doesn't just do one or two dives and then drink beers on the deck (which, quite frankly, sounds awesome to me). Oh no. He does four or five dives every day, and when the sun goes down, he goes on night dives. And when they're tired of diving, they go on serious hikes, "I mean, serious hikes. Not this walk in the park shit." (He apologized the first two times he said "shit," then gave himself free rein.)

He asked me two questions about myself.

I know, from reading Men Are From Mars, that guys will go on doing that, thinking that it's making you happy, unless you give them a clear cue that it's not. I had that damn squinty smiley expression on my face, so I was giving him a clear -- and totally wrong -- clue. And I just wasn't interested enough to interrupt.

Perfectly nice guy, but not at all the right fit for me.

Lessons learned:

  • "Music" is not really something in common
  • Trust my instincts a bit more: I need to give people a chance, but I also need to listen to my gut. I know what doesn't work, so I should rule those people out.
  • It can be strangely difficult to get away from an afternoon date.
  • 43 is my new cut-off age.
6Mar/090

Vicarious experience of reading my vicarious blog

A friend of mine recently had his online identity stolen -- as in, someone took his photo and name and posted a profile to a gay dating site. He recently found out about it when the online boyfriend Googled him and found the real guy, M., who is straight. The online boyfriend sent my friend 56 pages of IM conversations between him and the fake M. M. sent it to me.

I had two thoughts:

  1. It's super neat to be able to peek in on two people falling for each other. It's such an amazing feeling to go through that yourself, but it's almost as fun to be on the periphery, watching it happen.
  2. After about page 3, it became clear that the impersonator was hiding something, which made me even more angry at the false M. The online boyfriend seemed like a nice guy who is looking for love and acceptance. There are few things worse than letting yourself be so open to someone and let them in then finding out that they betrayed you. I hope the online boyfriend recovers from this.

Two more thoughts:

  1. Be careful when dating online! If someone doesn't tell you his first name, run away!
  2. I can now kind of see why people besides my friends read my blog. There's something really sweet about going through those vicarious experiences.