12.07.09
Coffee is for closers, aka closing the deal | Baby step #4
“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:
- 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.
- 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.
Present your best self | Baby Step #3
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.
11.08.09
Eye contact | Baby step #2
When I read that a woman needs to make eye contact with a guy 13 times before he’ll approach her, I had a dating epiphany. Though, like most of my dating epiphanies, it takes a long time for me to go from realization to implementation.
A couple of months ago, after my band played a show, I noticed a guy checking me out. I initially had to congratulate myself on recognizing that he was doing that. (My general obliviousness is my biggest dating obstacle.) But then I thought, “Wait a second! I can, with my actions, actually encourage him to come talk to me!” So I made eye contact. Twice. The second time, it was like I had sent out a homing beacon. The guy came right over. Nice!
We chatted for a bit about various things (nothing particularly memorable two months later). I don’t know how old he was, but he had the awkwardness of a guy in his mid-20s, complete with goofy nervous laugh punctuating comments that weren’t really funny. It’s OK, though. He might have been nervous and I was nervous, and he was nice and I was nice, and it was a pleasant conversation. No sparks, though. He said he’d come see another show I was playing that Saturday, he asked if I wanted to hang out before then, I said I couldn’t before but I could after. He seemed disappointed and asked for my number, which I’m sure was his way of making a graceful exit, and I was fine with that. I think we each realized, after talking to each other for about 5 minutes, that nothing was going to happen.
But the end goal wasn’t the point. The point, for me, was that I made eye contact with a boy! Yes, this is stuff I should have figured out in high school, but for some reason I haven’t. Baby steps.
10.23.09
Date weight and “hot girl” jeans
Viv, over at Bread and Boys (my new favorite single-girl blog), just wrote a really great post on date weight. She writes:
But the term “date weight” takes the form of many names. Among some girls it’s also known as the “Hey baby” weight. It’s different for every girl, but it’s the size & shape you achieve when random people on the street eye you once-over and yell “Hey baby!”
Last summer, I was on fire. Well, as “on fire” as I get. Dudes were all over me, as much as dudes are ever “all over me.” But I dated two guys that summer and smooched a third that year. I haven’t done that well since college. I’ve been wondering why this year, I’m so off my game. Or rather, why I have no game. When I read Viv’s post, I realized it’s because I’m no longer at my “Hey baby” weight.
Like her, no one in their right mind would call me big. But I was running a lot more last year. I was fit and strong, and, probably more important, I was confident–I knew I looked pretty good.
The barometer of my “Hey baby”-ness became my pair of skinny “hot girl” jeans. When I bought them, they were like a trophy–a recognition of my physical accomplishments. I wore them out a lot last summer, and I looked gooooooood. By November, I could fit into the hot girl jeans, and they looked…fine. I wore them to a holiday party in December and kept asking my friend, “Do you really think I can pull these off? Maybe I should run home and change.” (Yeah, I was that girl. Annoying.) By January, they were not to be worn in public.
And that’s about where I’ve been ever since. Time to start hitting the pavement! I need to get my game back. Time’s a-wastin’.
Photo by bluryee. CC 2.0.
09.14.09
Talking to Strangers | Baby Step #1
At brunch the other week, my friend KP and I started talking about dating, as we always do. She told me about a friend of hers who had just moved to Chicago from San Francisco. “You know what’s different about Chicago?” he said on a recent visit back. “When you go to bars there, you don’t just talk to the people you came with.”
That is so true. I remember one night when KP and I were out with a group of other single girl friends. We were going to meet boys. Our friend T., who has a longtime boyfriend, found a spot where we all could sit–on the kegs in a side room–and we all rebelled. No guy is ever going to talk to us back here! But we were looking at it at too micro a level. No guy was going to talk to us, yes, but not because we were hidden away. It’s because we were in San Francisco.
It’s not that people here are unfriendly, it’s just that it’s not a “talking to strangers” culture. It’s a “I go out to have a good time with my friends, and, maybe, their friends” culture.
I realized what I needed to do: I needed to learn how to talk to strangers.
Here’s the other insight about dating in San Francisco that I recently gleaned from a friend: no one’s got game. “You go to New York, you go to L.A., and guys know how to ask for your number,” she said. “Here, all the girls are all third-wave feminist about it. They try to be interesting.” At first, I wanted to disagree. But after about five seconds, I knew she was right. I try to be interesting. I talk about New Yorker articles and how effed up Iceland’s economy is. That’s interesting and challenging and life-partnery. But it sure isn’t sexy.
So I’m starting a whole new tactic with this blog. I realized that–like sports, like learning an instrument, like anything, really–if I want to improve, I need to work on my fundamentals. I used to have OK game. Now, I have no game. I need to get game. Talking to strangers is step 1.
Tonight, after a slog of a day at work, I decided to take a detour on my way home at my friend’s bar. I went in, said hi, and immediately A., a fellow musician who I’ve met before, said, “Sit down, have a beer.” So I did. We talked about music, remote islands, pirates, the East Coast (he’s from Pennsylvania). It was fun. Then he got up to start playing the house piano. Mission accomplished.
I was about three-quarters done with my beer and thinking of heading out when J. sat down. Out of the corner of my eye, he seemed kind of cute. I saw he had a hardbound book. OK, I can do this, I thought. “What are you reading?” I finally asked. We started talking about language, linguistics, where he’s lived, where he lived with his ex-wife, and where I’ve lived. And, also, his girlfriend and her two kids. After a while, I had to head out and he had to head out, so we introduced ourselves in that oddly comfortable yet still odd way that comes at the end of a long conversation.
As I hugged my friend goodbye, he said, “Did you get that guy’s number?” I told him about the girlfriend and kids. But it wasn’t about that. I was pretty excited about the basic, though boring, achievement of just talking to someone I’ve never talked to before.
Baby steps. Next up: remembering how to flirt.
07.28.09
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: HiyaWell, 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.
05.31.09
Email 18.1, Date 5: He’s probably not that into me
After posting about the guy who seemed happy to keep our online conversation strictly online, I worked up the nerve to see if his schedule had opened up. He responded, asking me about some things I had mentioned in my last email. He also said that he’d be in touch on Wednesday to let me know when he was free.
Ball’s in his court, I thought. If he doesn’t email me, then fine, he’s clearly just not that into me. Wednesday night, I logged on to OKCupid — no email. So I checked out his profile, wondering if I was really that into him.
He was online.
Now, on Match or whatever, it doesn’t matter. You could completely stalk someone, and they wouldn’t really know. But OKCupid pops up a little note: “[username] just checked out your profile.” Caught in the act. I panicked, hastily closed the window as if that made a difference, and felt somewhat foolish.
The next day, I had an email from him. We made plans to meet for lunch, joked around a bit, and sent longer, more frequent emails to each other over the course of the next couple of days. At one point, he wrote, “You are a fantastic writer!” (He mentioned in his profile how words are important to him.)
We met for lunch, and it was immediately comfortable talking to him, though the conversation still had some of the first-meeting nervousness. He makes great eye contact. We dove right into a fascinating discussion on print and online media, ordered tacos, and talked some more. The conversation did peter out a bit, but my “I can only do an hour” lunch turned into about an hour and a half. I walked back with him to BART, and he gave me a nice hug goodbye, saying, “I had a great time. I’d love to come see your band sometime.”
That, friends, is the kiss of death. If he was interested in me, he probably would have said, “Let’s do this again,” or something. It’s sort of the musician’s equivalent of hearing, “I’ll call you” — an implied continuation of the relationship without any plan to actually follow through. Wanting to be one of 50 or so people in an audience when I’m onstage at a gig that is likely to be weeks away felt like a romantic brush-off. But who knows? He does like music.
I sent him an email before I headed out of town for Memorial Day weekend reiterating that I had a fun time. We’ve exchanged a few emails since, but I don’t really get the feeling that he’s that into me. He seems like a nice guy, though.
And for those who think I’m prejudiced against short guys, he’s 5′8″ and I would definitely meet up with him again. So there. :)
Missing Signals: Eye Contact
Dating, like anything, has its ups and downs. For me, if it were weather, it would be like highs of 70 and lows of about -30 plus a wind chill. Or to borrow my (happily coupled) friend Lessley’s expression, “Dating sucks until it doesn’t.” Constantly focusing on the subject by blogging about it is partially to blame, as is my friends’ questions about when my next post is on the way (you can’t force genius, people — kidding!). But I have to admit that by focusing on it so much and by putting my personal life out there for people to comment on, I have figured out a lot in this past year.
A lot of forces have recently joined to help me begin to confront my number one obstacle, namely sucking at reading guys’ signals. My problems are twofold:
- I think guys who don’t like me actually do like me. (Evidence 1. Evidence 2.)
- I don’t know when guys are actually interested in me.
Now, at some point since I’ve started blogging, just based on law of averages, there has to have been a couple of guys who have been interested in me. Odds are, one or maybe even more have been guys I was or would be interested in. So how did I miss them?
I recently started reading this blog on Marie-Claire’s site, a Year of Living Flirtatiously. The author, Maura Kelly, posted something about how a woman needs to make eye contact with a guy roughly 13 times before he’ll approach her.
13 times.
Really. 13 times.
That, in a nutshell, is why I suck at dating.
I went out for happy hour with the bros on Wednesday, and D. was staring past me at one point. “Are you watching the game or is there a hot girl back there?” I asked. “Watching the game. I have a sixth sense for spotting hot girls, though,” he said. I don’t. I don’t even notice other people in the bar. When I hang out with my friends, I only really pay attention to them.
I had all this in mind on Friday night when I went out with two girl friends, R. and A. A guy at the end of our table looked over toward me when they were up getting beers, and I met his gaze. The feeling was so foreign to me. I honestly couldn’t remember the last time I’d done that once at a bar, let alone 13 times with the same guy.
So my next step is to do exactly what Maura did when she found out about the magic of the baker’s dozen: test-drive that shit. When I go out, I’m going to practice making eye contact with interesting-looking guys. I think this strategy might also help when I’m out with the bros, too. I mean, after 13 looks to another guy, I’m clearly not dating any of the guys I’m with, right?
05.10.09
They only like me for my laugh
On Cinco de Mayo, I was chatting a bit with D., my newest bro. He made a joke, we all started laughing, and he said, “There it is!” “What, my laugh?” I asked.
“Yes! When I first met you, your laugh freaked me out,” he said, “but then I really liked it.”
“And then you wanted to make me laugh just so you could hear it?” I said.
He pointed right at me, shocked that I had read his mind. “Exactly!”
In that moment, I suddenly understood, at least partially, why I constantly misread signals. Guys try to make me laugh because I have a really loud laugh (as anyone who knows me or has heard the podcast knows). There’s nothing more validating to your sense of humor than to have someone laugh uproariously at your joke. I do that for people.
In fact, at my friend Liz’s wedding, our friend Dave came all the way over to my table at one point to make some joke. He looked disappointed when I only laughed a little. “I bet those guys that they could hear your laugh all the way over there,” he said, a bit crestfallen. He wasn’t disappointed that I wasn’t laughing; he was disappointed because he had just lost $5.
When a guy repeatedly tries to make me laugh, I think he’s interested in me. But no. It’s purely for their ego. Or, alternately, to win a bet. I don’t factor into the equation at all except that I happen to be the vehicle for my obnoxiously loud laugh.
I feel oddly better now that I’m aware of this, even though it means that I was misreading the one signal I thought I could actually read. Why did no one ever teach me this stuff?
05.03.09
I’ve become a bro
Two years ago, I started working at a very social tech company, and all of a sudden, I had all these amazing guy friends my age. Around the same time, all my girl friends were getting engaged, getting married, having kids, or settling down with their boyfriends. So after work and often on weekends, I hang out with my bros.
In our Sunday Irish Breakfast Football Club (basically, an excuse to meet at a pub, start drinking at 10 AM, and watch football all day), I was often the only girl. Ray, from the podcast, has me in his “Bros” group on IM. Gary calls me Brosephina. And I get invited to (some of) the bros nights out (if it involves sports, strippers, or more serious broing out, they wisely don’t invite me).
I kind of like it. I mean, I love these guys, so I love hanging out with them, but I also like being one of the bros. Lately, though, I’ve seen the downside of being a girl bro.
A couple of weeks ago, I went out for a Friday happy hour with some friends, and I was joking around with one of the guys there, who, by the way, is ridiculously hot. Like insanely good-looking. At one point, after I had been talking to another guy, he put his arm around me for a second. I wondered if it was the “marking his territory” move that guys do.
That Saturday, I ended up meeting up with that same group, and at the end of the night, he said, “It was really fun hanging out with you this weekend,” gave me four fist bumps, a high-five, and a hug. I didn’t really read anything into it (he was pretty done-zos by that point and I’m absolutely not his type), but still.
I saw him again at a happy hour the next week, and he immediately started talking to me about the difference between flings and hook-ups. And that’s when it became clear to me: I’ve become a bro, even to guys who don’t know me that well.
This is not a good development for a number of reasons:
- I am horrible at accurately reading guys’ signals. I always think guys who just want to hook up actually like me and that guys who like me just want to be friends. When D.D. and I were hanging out as friends, he said, “So, are you having fun hanging out?” I thought, “Oh, he wants to make it clear that he wants things to stay as they are, that we’re just friends.” No, he meant that he wanted to hang out more. So when he went in for the kiss at the end of the night, I went in for our standard hug. Faces collided, awkwardness ensued. Although, that did make it my most memorable first kiss.
- How am I ever going to meet a guy when I’m surrounded by bros? Before the BRT recording session on Thursday, I met the bros at a bar down the street to watch the last two (of three) overtimes of the Bulls-Celtics playoff game. It was me and three dudes, watching sports. Even if some guy gives me cred for watching sports, the natural assumption is that I’m dating one of the three. It’s like that Seinfeld episode, when some guy hits on Elaine when she’s out with Jerry, and Jerry gets offended. They guy didn’t know they weren’t together, so why would he assume they weren’t? Most guys would guess they were together.
I do love my bros, but I also need to make more of an effort to hang out with my dwindling pool of single girl friends. Also, I need to stop immediately referring to guys by their last names. That might be part of the problem.

