100 Emails, 20 Dates

Online dating hasn’t been going so well for me. This is brought into dramatic relief when my friends sign up for the same sites I’m on and immediately get winks, messages, and the seemingly inevitable dates as my profile languishes in obscurity.

Initially, I decided to take my profile down out of frustration. I gave up on online dating. But then I read that I’m in the Zone of Greatness. And I thought, “OK, ONE more chance.” But this time, I’m going to do it differently.

Ever since I heard of that book Marry Him by Lori Gottlieb, I’ve been troubled by one thing that she says: that things we think are quirky and endearing are actually really annoying to others. I think my online dating profile could be full of these potential landmine.

So this time, I’m going to try to make my profile not be a dating minefield. I’m not leaving it to chance or my instincts. I’m doing it by the numbers.

OK Trends, the number-crunching official blog of OK Cupid, has posted a wealth of data-driven dating advice. And I’m going to follow it as closely as I can.

1. Successful profile photos. Smile, look sexy, and yeah, maybe show the cleavage.
2. What to say in a first message. Starting it off with “How’s it going” gets more responses than “hello.”
3. How long to make that first message. The data says that a 360-word or longer email will scare a dude off.

I’m going to try to track down more and put this all to the test. I’ll let you know how it goes. First step: changing my username. My current username is boring and speaks to a hobby. My new username speaks to a trait and also implies that I am a happy person. I think this is a good move.

Also: Matt, from Online Dating Paradox, is doing a 300 emails in 30 days online dating challenge. If I can get my new profile up, I might join him. But even if I don’t, I’ll be cheering him on!

OKTrends, the fascinating official blog for OKCupid, recently did a post on dating preference and age. In large part, it confirmed my long-held suspicion: I joined online dating sites too late. Dudes rule me out because of my age (36). Although the male-female ratio for my age group should work in my favor, the “male fixation on youth” does not. Though I fit in a 32-year-old’s allowable date range, men mostly contact women in the lower end of their allowable date range, but they also contact women much younger than that. Those 32-year-olds? They email women as young as 18 (say it with me: ew!).

The post continues to depress women in their mid-30s, until then, the author turns it all around to show why women my age are EXACTLY who younger guys should be dating. Yeah, I am squarely in the middle of the Zone of Greatness.

Why all guys should want to date me, courtesy of OKTrends.

The post goes on to analyze factors guys should care about. Oddly enough, they’re also things guys with younger girlfriends often complain about. Dump those girls! Date chicks in their 30s! We’re self-confident! We’re happy! We not squeamish about sex! We’re OK with dating dudes if it won’t lead to marriage (96% of 36-year-olds are OK with it vs. 62% of 18-year-olds)!

Also, we’re just as hot as those frigid, fragile 20-somethings:

Many of you are probably scoffing at the idea that many 35 year-olds are as attractive as many 25 year-olds, but there are social factors at work that you might not consider as you go through life making judgments. Most importantly: nationwide, thirtysomethings are much more likely to be married and therefore much more likely to have stopped optimizing their attractiveness. So the typical 35 year-old woman you see out in the world isn’t representative of the single 35 year-olds who are still dating and looking good.

I look good! My single friends look good! Y’all don’t know what you’re missing. Read the complete post. It’s so interesting.

My friend Sonia just blogged about Booty Pop. Apparently, no longer just a plotline on Laverne & Shirley, there really are butt enhancers (and underwear! All in one! Awesome!). I find it kind of horrifying that these tiny, twig-like girls are padding themselves back into more feminine body shapes with underwear, bras, and, if need be, silicone. Just rock the body you’ve got, ladies.

See, I have a booty. I have a booty despite the fact that I work out, I eat healthy, and yeah, I wear a size 0, 2, or 4 (depending on the store). My booty is there no matter how great or poor shape I’m in. I used to be self-conscious about it. I always thought of it like my little pooch of a belly, something I had had since puberty and, though I should try to lose it, I was never going to, short of spending eight hours a day for the rest of my life working out with Jillian Michaels. Slowly, I started to notice that guys I dated, um, appreciated it, but I didn’t really think anything of it. Just because a guy likes a girl’s body part doesn’t mean it’s a good one. It means it’s there and available.

My life changed when my friend Mary taught me how to drop it like it’s hot.

Dropping it like it’s hot is an incredibly empowering move. Your booty is out there. You need to like it. You need to own it. You need to be proud of every curve–even those dimples of cellulite. You know why? Because after you drop it down low, you are going to pick it up slow, and you are going to be sticking it way the heck out. (Picking it up slow also helps you keep your balance.) When you come back up, you know that everyone is going to be looking at your ass, partially because you just slapped your hands against the ground to call attention to the move, and you need to own that moment. You need to want their eyes to go there. Make them linger.

Dropping it like it’s hot about 500 times in one night made me realize: I have a pretty nice ass. (Also, dropping it like it’s hot kills your quads. Stretch before you go to bed.) It was so empowering to realize that I had this hot-girl feature that I never realized I had. And it was right behind me the whole time.

The point is: Ladies, find what’s sexy about the body you have, and then ROCK IT! Forget this padding stuff. Just get the rolly on your arm and drink Chandon.

You can learn it too! Here’s a British dude offering a very good, though long-winded, explanation:

Note: I was going to try to find an uncensored version of the Snoop Dog video, but then I thought it was super funny to have the censored one.

I’m supposed to get notified if you’re a first-time commenter, so I can approve your comment. But for some reason, the notification isn’t working. I’m looking into it.

For those of you who missed her comment in the delay, Naomi updated us on the awesome Craigslist sugar daddy dude. So great.

This month, I was looking forward to my band’s regular gig even more than usual. See, last month, my bandmate, the hot surfer dude (who, it turns out, graduated college 10 years after I did), and I closed out the bar, which is always a fun thing to do on a Monday night. R., the surfer, is a regular there, so I was hoping I’d get to flirt with him again. I don’t really think that we’re a good fit, dating-wise, but ooh boy, I sure want to kiss him.

He was there, sitting at the bar with another surfer type. I saw him as I went to pour myself a beer, but he wasn’t looking up. On my way back, I caught his eye. “Hey, N.,” he said. “Hey, Matt,” I replied, and walked backstage.

I talked to him for a second at the set break, but he was gone by the time we finished. “That was nice of R. to come. Did he leave already?” my bandmate asked.

“Oh no!!!” I said, doubling over from embarrassment. My friends asked what I was talking about. “R.!! I called him Matt!”

“You can fix that,” the bartender said. “Just say Matt was your first boyfriend. He’ll be bummed, though.”

“Why?”

“He really enjoyed talking with you last month,” he told me. “He really enjoyed talking with you.”

I don’t know if it’s bad luck or karma or something in the universe wanting me to stay single, but during the occasional periods when I have good boy luck, it’s immediately followed by some stupendous act of self-sabotage. You know, like calling a really nice guy who I genuinely enjoy hanging out with and definitely want to smooch by the wrong name.

Even worse, I did it again. My friend K. invited me to see her boyfriend, D., and a couple of other friends spin. She sent me the invitation, and I said, “Oh, I didn’t know you knew B.” It turns out she and D. were thinking about trying to fix me and B. up. It turns out I had a small crush on B. when I met him briefly about ten years ago. He, really, is exactly the kind of guy I should be dating.

The night of the show, my friend J. and I went out for rum drinks at a pirate-themed bar. After two exceedingly stiff drinks, I was feeling pretty good: buzzed enough to dance, sober enough to not make too much of a fool of myself. We went to the show, we ordered two more drinks, J. left early, and as I walked back in, wondering whether to stay or go, I passed B., who K. had introduced me to earlier.

“Hey,” I said, touching his arm to get his attention, which I thought was a smooth move. “Have you seen K. and D.?”

“They’re all the way up in the front,” he said.

“Hmmm. My friend just left, and I’m trying to decide if I want to make my way all the way up there,” I said. And then we started talking. It was one of those fun first conversations when there are no awkward pauses and you learn so much about each other in a short amount of time.

Maybe it wasn’t such a short amount of time. At one point, D. came up and told B. that it was his turn to spin, but D. could do the set if he wanted. B. said sure.

It was loud. So loud that there was no chance of interrupting each other because when one of us would start speaking, we’d have to move our mouth to the other person’s ear in that pleasantly forced-intimate way. We talked about country music and our shared admiration of the Nashville hit machine. There aren’t many guys in San Francisco like that.

It ended when he had to go to the bathroom and I had to get water. After I found K. and the glow of the conversation wore off, I realized something. I had been cursing like a sailor the entire time. Eff! <=(This is how I usually curse.)

It feels like it’s been so long since I’ve met guys who I like and who seem potentially interested in me. And it’s so frustrating that I’m so woefully out of practice that I keep shooting myself in the foot instead of making a decent first impression. Argh.

This, in a nutshell, is why I would never bring a guy I just met back to my house:

January 18

Theft — 1:00 am. 4200 block of 26th St. Victim met suspect through a dating service. He invited suspect into his home and passed out. When he awoke, his date and his property were gone.

Though it does make me wonder if “dating service” is a euphemism.

When you have friends–especially good friends–of the opposite sex, the “What if?” thought is going to pass through your head. If, when you have that thought, you realize that you’re attracted to the friend, it’s going to become a crush. In college, I dubbed this the When Harry Met Sally syndrome. I don’t think of it as a bad thing. After all, isn’t this the ideal? Finding a partner who’s your best friend too?

On Friday night, I went to see It’s Complicated with friends, then we met up with some of the bros at a bar. They had been drinking since happy hour. We got there at midnight. A bunch of people went out to dance, and P., who I had a friend crush on earlier in our friendship, said, “Put down your things, we’re dancing.” I put down my coat and kept my purse on my shoulder. “Put down your bag,” he said. I said, “No, it’ll get stolen.” He asked what would be the worst thing to lose, and I said my keys, because then, after losing everything, I wouldn’t even be able to get into my house. “Hand me your keys,” he said.*

“I hope you know this doesn’t mean we’re sleeping together tonight,” he said as I handed him my keys.

Insert sound of record screeching to a stop. “What?” I said, mind racing as I turned back around to close my bag. “Where did this come from?” I wondered. But also, “FINALLY! A chance to find out if he ever liked me.”

“So the thought has crossed your mind?” I asked.

“So many people have asked me why we’re not dating,” he slurred.

“Like who?”

“So many people,” he repeated, in that frustrated tone drunk people have when they’re fighting their beer-soaked brains to try to communicate something genuinely important. “I love you, N. I mean, I really love you.” He gave me a huge hug, then kept one arm around me. He gets really lovey when he’s bombed. “I have mad love for you. You are one of my favorite people. I want you to know my family, my friends–I don’t do that with just anybody.” He stopped and gave me another giant hug. “But,” he began regretfully, leaning in closer, “I like Asians.”

Which I knew all along, and which is why, when R. insisted that he liked me (when he was in another drunk lovey state), I knew he didn’t.

At first, I was disappointed. The guys who I think would be a good fit with me either don’t find me attractive or just want to hook up. But today, I woke up and saw it differently.

The three friends I’ve had crushes on in the past two years have a lot in common: they’re all really smart, fun, thoughtful, and, in general, exceptionally good guys. But they all represent different things:

• A.: One of the smartest people I know. It can be a challenge to keep up with his brain, but it never feels like a competition. I love people like that.
• J.: There have been times when I’ve started to freak out about things, and he just puts his hand on my shoulder. Suddenly I feel calmer. Very subtly, he accepts where I am emotionally–without judgment–and points me in a more productive direction. He’s the one who made me realize I need this kind of emotional balance in my life.
• P.: I’ve had deep conversations with all of these guys, but P. and I have been really honest with each other, and I love that about him. But he’s also really, really fun. When he rallies people to go out, you know you’re going to have a great time. He’s more outgoing than me, and being around him help me be more outgoing.

Those guys’ reactions to me have been equally telling:

• A.: Respects me for my intelligence and sense of humor. I feel smarter and funnier around him, and I feel safe enough to take risks, because it’s OK to make a joke that bombs around him.
• J.: Totally had the hots for me. It was disappointing that that was all he felt, but I’m trying to look at the positives here. It was nice to be wanted.
• P.: Sees me for who I am and loves me for it.

So what I need, really, is these three guys rolled up into one. But the fact that I’ve found three great guys over the past two years who are almost perfect for me means I’ve figured myself out enough to know what kind of guy is going to bring out the best in me and what kind of guy I’ll be the best partner for. Now, I just need to find him.

If you see this bag (only with 2 straps instead of one), please let me know

Full disclosure: This post was equally inspired by the Friday-night conversation and a Taylor Swift video that Kristin posted. Which does of course beg the question, why do I so closely identify with the emotional life of an 18-year old when I am twice her age? (That was a painful sentence to write.)

*My purse was, in fact, stolen, somehow while we were standing right in front of it. I should have trusted my instincts. If you see a bag that looks like this photo (right), but has two straps, it’s mine. Seriously, no one else in San Francisco has this bag. If you can get it back, I will pay you a reward.

Horrible subject lines from many, many guys.

I stumbled across Matt from PlentyofFish’s great blog post on terrible subject lines, which describes my online dating experience to a “T.” (Then I commented on it, and then I realized it was from last year. Still, timeless.)

“I’d wish you good luck, but you wouldn’t know what to do with it if you got it.”

I was passing by my favorite bar tonight, so I decided to stop in for a happy hour beer. I figured if there was no one else to talk to, I could talk to my friend, who tends bar there most Mondays.

There had been a guy standing outside who looked like he could be my friend’s younger brother: same surfer look, blond hair, and plaid shirt. He came back inside and sat down next to me, then immediately got up and start affixing something to the door. Me, my friend the bartender, and a couple other guys started talking about fried chicken. You know, as you do with strangers at a bar.

Hot surfer dude sat back down, and we started chatting. It turns out he’s from my home state and not that far away. I think he’s right out of college. (My 15-year reunion is in May.) We talked about fake IDs, he told me his foolproof method of faking the ID from our home state (a key element is having a friend who works at Blockbuster, because they use the same lamination technique), what we did for a living, NASA and rocket scientists, the cellophane he taped over the broken window in the door, other random things. Did I mention he was hot? And nice? And hot?

I realized, however, two things:

1. I have no inner cougar. Some girls do, some girls don’t. My friend J, who calls this kind of hot young thang a “puppy,” does. I admire that. A lot. I mean, it would be kind of fun, right? It seems like it would be fun.
2. I am not a closer. Even if, at some point, I thought, “I want to smooch this guy” or, perhaps, “I want to see this guy again,” I have no idea how to get the conversation headed in the “exchanging phone numbers” direction.

I suppose “closing the deal” should be baby step #10 or something, but I’m really so hopeless after the eye contact thing that I don’t know the proper order after that. So I apologize for the non-sequential baby steps. Expect more of the same. #22 will probably be “Introducing yourself” or something.

So how does one close the deal? Should a girl let a guy do that? If so, how does she pave the way? Thoughts?

As a sidenote: Ooh, young Alec Baldwin. So hot. So angry.

One piece of dating advice that I think is really, really true is to be yourself, but be a better version of yourself. This isn’t to say that you should mask who you really are or pretend to be something you’re not in order to make a good impression (thus setting yourself and your date up for disappointment when the real you inevitably reveals itself down the line. It’s to be the best you, the good you, but still the real you.

Still not buying it? Let’s use an analogy. Sometimes, on weekend mornings, I leave my house with bedhead. I don’t put on makeup. I wear the jeans and t-shirt I wore to the bar last night and they may still smell faintly of beer or smoke. I can’t tell, because I smell faintly of beer or smoke. That’s three-months-in me.

When I go on a date, especially a first date, I make sure my hair looks like how I want it, not how it ended up that day. I reapply makeup. I wear something flattering. I don’t make myself look like something I’m not, but I put my best foot forward, physically. Although that’s not the real me everyday, that’s the real me on my best days.

It only makes sense to put your best foot forward, personality-wise, too, right? So why is that so hard to do?

A friend fixed me up on a blind date a few weeks ago. “Before you meet him, I need to brief you on O.,” she said. “He’s very dry. For the first few weeks I knew him, I thought he hated me, because he just didn’t talk. But now he’s one of my dearest friends and he talks my ear off.”

Armed with this information, I met him for a beer. She was right. He was very dry. Very. I was working very hard to get him to talk and to open up. He didn’t ask me many follow-up questions when I would talk about myself and seemed uninterested in what I had to say. (He didn’t even seem that impressed that I was in a band, and let’s be honest, if I don’t wow a guy with that, the “life history” bag of tricks” is pretty damn empty.)

So I kept asking him questions. I filled the silent spaces. I made him feel comfortable, or tried to. And at the end of the night, he asked if I wanted to hang out again. I said sure.

As I thought about it after, I felt frustrated that I was working so hard. I mean, come on! It’s a first date! Ask the girl some questions! Is this a sign of what’s to come if we date? Am I going to have to do all the work? And I kept coming back to my friend’s warning. That’s what made me agree to see him again, because to be honest, it was a fine evening, but it wasn’t fun. But he was opening up toward the end, and he was a nice guy. So why not?

And then I realized that as much as he wasn’t being the real him, I wasn’t being the real me. I was appalled at my somewhat forced laughter that night. I’m normally fine with pauses in conversation. I emphasized parts of my life that normally, I would not emphasize. I wasn’t my best self. I was an annoying first date self. That helped put it all in perspective for me. I wasn’t just giving him a second chance; he was giving me a second chance.

So I hope I make some progress on this step in “date” #2 (it feels like too much pressure to call the “getting to know you” evenings dates). We’ll see.