iPhone: So intuitive, even someone you're hitting on in a bar can figure it out

One night last week, I met my friend J. for a drink (or three) at a bar (or two). Between bars, we stopped and got sausage sandwiches at Rosamunde's, then took them next door to Toronado, a divey bar that has probably the best beer list in all of San Francisco. Of course, the bar was full. Not packed, but full enough that we knew better than to try to find a table all our own.

"We could sit with those guys," I said, gesturing imprecisely and awkwardly with a beer in one hand and a sausage sandwich in the other. J. went up to two guys at the table right in front of the one I meant.

"Do you mind if we share your table?" she asked. They said that their friends were coming back in.

"How about that table behind them?" I said. Those guys did not have any returning friends, so we sat down, starting eating our delicious sandwiches, and started chatting. One of the guys had just quit his job in a now-or-never moment in order to pursue a dream project (he wouldn't tell us what it was, despite the fact that I offered to sign an NDA on the back of a bar coaster). We raved about the pastries at Tartine and envied the other guy, who lived around the corner from that bakery. It was a fun night--the kind of night that made me deeply appreciate those times when people are willing to share their space with strangers. It opens up some fun conversations.

J. and I, still employed, got up to leave around 10. The cuter of the two guys asked if we'd still be there when he got back from the bathroom, and I said yes. As he left, his friend pulled a GENIUS move! He said, "OK, let's exchange contact info," and passed J. his cell phone so she could enter it herself. SO SMART! I handed that guy my iPhone, entered my info in his, and then his friend came back. I handed him my iPhone, and said, "We're doing a do-it-yourself contact info exchange."

Droid: Is that a Home key or a left arrow? And why does Menu look like a flag?

He handed me his Motorola Droid. I was befuddled.

A slight (possible) disclaimer: I am a diehard Apple fan. I'm writing this on a MacBook Pro. I love my 1st-gen iPhone, which I am back to using after my iPhone 3GS was stolen. I'd be lost without my iPod. If I had an extra $500, I would TOTALLY buy an iPad (though, since I don't, I will wait for the second generation one). But still, I did kind of feel that this was a use case the Android UI designer hadn't thought of.

First, I couldn't figure out how to get the keyboard to open. Then, in horizontal mode, I couldn't read any of the buttons. "Hit the Home button," he said. After staring stupidly at it for a few seconds, I realized that he meant the one that looked like an arrow (win for Apple for designing a button that looks the same in both horizontal and vertical orientation). The screen showed one field, for "Name," and one button: "Done." Would "Done" take me to the next field? I clicked that, then ended up in his address book, feeling like I was totally violating his privacy. I scrolled to my name (of course, toward the end of the alphabet), then couldn't figure out how to get into my record.

"Click the Menu button," he said. (By this point, I felt like a total idiot. I am normally very good with technology.) The "Menu" button probably looks menu-like when holding the screen vertically, but in horizontal view, not so much. I finally managed to enter my name, phone number, and email. I also probably managed to convince him that I was a total dunce, and now that he had my info, he wouldn't want to contact me. Tant pis.

This whole episode taught me a few important lessons:

1. One of the best ways to meet people is by sitting with them: at the bar, at a communal table, or asking to share their table.
2. The whole "DIY give me your number" thing is really brilliant. If everyone at the table is doing it, it takes the pressure off. It's just new friends exchanging info. Also, if you forget the person's name, it's no biggie. They enter in themselves. You look at it when they hand back the phone, and say, "It was nice talking to you, ______." Genius.
3. UI designers should really use this as a test to see how intuitive their UI is. For example, if I had seen that there was another field in the contact form, I would have scrolled down. But I didn't know I needed to scroll down. IT WASN'T ME, I SWEAR! IT WAS BAD UI!!!! I'm half-kidding, but I'm mostly serious.

Editor's note: As I was looking for screenshots to illustrate the weird contact screen, I couldn't find a single image of Droid Contacts in landscape mode. I am taking that as further evidence that Google/Motorola are hiding this error in UI design from the public, and that I am not a technological dunce.

Um....

I realized then that women can be our own worst enemies. Here we were, a group of good-looking, smart, funny, fun-loving girls who we were projecting the "Don't talk to us" vibe. It happens fairly often. It's not just uninviting; the body language says, "Back off." If a guy even thought of approaching us, he'd feel like he was stepping into the gauntlet. No fun.

Compare that to a recent night out with my (married) friend A. We went to get beers and sausages, saw that there weren't any open tables, so we joined a table with two other guys. And we all had a lovely conversation. No love connection for me, but still--I met two guys that night.

Wingwoman rule #1: Be open, not closed off.

Wingwoman rule #2: Talking about how hard it is to meet guys when trying to meet guys makes it harder to meet guys.

When I first floated the St. Patrick's Day idea to people, the idea was that we'd go to a non-Irish bar that always goes way over the top for St. Patty's (read: a place where you can actually have the experience you're looking for on March 17--a really fun night in a roomful of people who are also having a really fun night--unlike the Irish bars packed-to-the-gills with people who have been drinking since noon). Also, there was a 90% probability that a guy I was interested in was going to be there.

After the first bar, I said, "Let's go to [super fun non-Irish bar]!" The girls dilly-dallied. They wanted to eat. They didn't know what they wanted to eat. Or where. They finally decided to go to the neighborhood of the bar and find a restaurant there. They didn't know how many cabs to take. We decided on two cabs. It took a while to hail the cabs. When we got to the neighborhood, we walked around for a while until we finally agreed on a place to eat. There was a wait, of course. When we finished our dinner, everyone was tired and wanted to go home. So we did.

This is a crucial difference between chicks and bros. As my bro Ray Huff said, "Guys will totally help their guy friends get laid." They'll go to the bar. They'll buy the first round, leaving their bro more time to talk to the chick. They'll talk to the gay male friend of the girl--sometimes for hours. I've seen it happen. Guys support.

Girls do not. There have been many times when I've had to PLEAD with a friend to get her to come with me to a bar so I can hang out with a guy that I like. I know what you're thinking: "But then she went, right? What are you complaining about? It all works out in the end." No no no no no. Girls don't go. In the girl moral chain, friends come first, family comes second, work comes third, guys come fourth. So how do so many girls justify complaining so much about not having a guy?

Don't get me wrong: girls who always put guys first are not girls you want to hang out with for very long. But surely there's got to be some healthy middle ground, where girls take one for the team, chat up the less attractive or boorish friend, or--God forbid--stand by themselves in a bar for 10 minutes (thereby making themselves more likely to be approached).

Rule #3: If your girlfriend wants to chat up a guy, go with her.

Seriously, ladies, we need to help each other out. We're not getting any younger, and this sure isn't getting any easier.

In searching for advice on "How to Be a Good Wingwoman" for this post, I found only one article that was about helping your girl friends, not your guy friends. Thanks, Tyra.

I've gotten pretty good at telling who rated me: the oldest guy of the 9. But for one email I got in late January, there was a photo of a super cute guy. I thought, "Ooh. I wonder..." The hot guy had picked me! After we found out we were mutual matches, he sent me an email.

Date: Jan. 25, 2010
Subject: between becauses

Cute pics and mutual 4-star stuff aside, somewhere between Stevie Wonder, The Big Lebowski, the mandolin and wicked smahht, there is a good reason to at least say a real hello. Yes? Good times/places for you? I work for myself, so I'm flexible. You?

Hi

I love first emails like this. Friendly, casual, inviting, and--the thing I like most--he avoids the extensive emailing b.s. and cuts straight to the "let's meet up." His profile was the same way. He mentioned that he had a teenager, which sort of shocked me, but he seemed like a good, grounded, interesting person. I wrote him back the next day.

Date: Jan. 26, 2010
Subject: between becauses

I'm in. Thursday at 7 (or after) or Saturday afternoon work for me. I've been wanting to try the Rosamunde's on Mission. Though coffee or a drink would be fun, too.

The Stevie Wonder thing stuck out to me, too. He's so ridiculously good.

To be fair, I actually left off the last period. And that last line reads really awkward to me now. Eh.

He wrote back two days later, Friday, to say he was heading out of town that weekend and suggested we could get together the following week. I generally only suggest an actual date once, then if that doesn't work for the guy, I let him step up. If he's not interested, he won't suggest a date. I could have written back something short, like, "Have a great weekend. Next week sounds fine," just to show that I was still interested. But I didn't.

J. wrote me back a little over a week later:

Date: Feb. 5, 2010
Subject: between becauses

Geez, this life goes fast.
Okay, for reals.
You around tomorrow (Sat) daytime at all? Nice little walk and hello?
If not then, what's next week for you? Pretty much any day works for me up until 6ish. Open eves as of now are Tues and Thurs.
Let's just see.

I still liked the friendly, casual tone. The scheduling thing seemed a bit of a challenge, though. I find it a bit perplexing that people who work from home don't realize that we office workers can't just skip out early to meet someone for a date. Also, my phone had been stolen, and it had been a few weeks since I synced my phone calendar with my computer. I knew there were two appointments I was missing, but I wasn't sure how many others there would be.

Date: Feb. 7, 2010
Subject: between becauses

Hey, J.--

Seriously. This week and weekend flew by.

I love the idea of a walk. I think I'm free Thursday after work. (I don't mean to be flaky, but my phone--which has my calendar--was stolen a few weeks ago, and I just realized I have a couple of appointments that I never synced to my computer...)

Lunch might be a safer bet, though. Would you be up for meeting at the Ferry Building? I could do any day but Thursday.

I never heard back. He might have read my lack of response after he said he was going away as a lack of interest. Maybe next time that happens I'll write a quick, short, and sweet response.

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.

It's been excruciatingly frustrating. I haven't seen as much of my friends as I'd like, and I haven't had time to meet any boys. Or talk to the ones I have met, such as R., the cute surfer dude, who I called by the wrong name.

I actually ran into him at the bar one night more than a month ago. He seemed genuinely excited to see me. We chatted for a bit, and I said, "Hey, I wanted to apologize. I think I called you the wrong name the last time I saw you."

"Really?" he asked. "What did you call me?"

"I can't remember," I lied. "All I remember is that as soon as it came out of my mouth, I thought, 'I did not just say R.'"

He laughed. "I didn't even notice."

We hung out for a bit, some girl handed him her number, which felt weird, he went out for a smoke, and I suddenly became insanely tired. I walked outside, and said, "Hey, I think I'm heading home." We hugged goodbye, and I split, cursing myself for my chicken-shittedness.

Thus shamed, I finally figured out my line. I would stop by the bar randomly and say, "Hey, maybe we should intentionally meet up for a beer sometime." The only problem was "the stop by the bar" part. I haven't had a free Monday, the one night he is usually there, for weeks. When my plans this past Monday fell through, I finally got my chance!

I walked in, and he was at the bar, along with my band's current guitar player, A.. Perfect! I gave an enthusiastic hello, and R. greeted me a little awkwardly. There was an empty stool between him and A., but there was something about his body language that made me think he didn't want me there. I took the stool anyway and inched it closer to A. That felt a little less tense.

The bartender pushed his beer toward me. "Try this," he said. I did. It was a light-bodied porter-style beer. It was good. "R. made it," he told me. We all chatted for a minute about the beer.

Then sure enough, a few minutes after I arrived, a cute brunette showed up. R. immediately pulled out a bottle of his newly made beer. "This is for you," he said, handing it to her. They looked like they were on a date. Tant pis.

The great thing about happy hour at that bar is that everyone at the bar will join in on a conversation. We started talking about stinky colognes people wore in high school and everyone was laughing. R. laughed at a few of my jokes, and I saw the girl he was with unintentionally give me the evil eye. Oh well. I might be hilarious in barroom conversations, but she's got him. Good for them. He's a nice guy. He's probably better off with a girl his own age, anyway. And I need to act faster.

After O. and I went on our blind date, he gave me a ride home. (What a nice guy!) When he dropped me off, we talked about seeing each other again. It hadn't been a great date, but our mutual friend had warned me that he took time to warm up, and I was prepared to give it some time. Two or three weeks later, right before Thanksgiving, I got an email from him:

Date: 11/28/09
Subject: Greetings from Hawaii

Hi N.,

Just a quick note to say "Hi".  Sorry for being out of touch.  This trip has been crazy.  The windsurfing conditions have been unreal - so good that we decided to extend the trip another week.

How have you been?  Doing anything fun for the long weekend?

O.

Oh! He'd been out of town! He hadn't mentioned that. I sent him a friendly but short email the next day, asking if he had mahi-mahi and all the trimmings for Thanksgiving dinner. A week and a half later, he sent me a really nice email, in which I could start to see a glimpse of what my friend saw in him.

But nearly a month and a half had passed since our first date, and he was only available to meet up on weeknights during December. My weeknights were booked with Christmas parties and work. I could have--and probably should have--cleared my schedule one night to meet him. But I still felt burdened by the effort I was putting in, especially when his responses were so tepid.

I think, ultimately, that the blind-date setting was a bad way for us to meet. Maybe I'll run into him at one of our mutual friend's events. I hope so. I'd like to get to know him better, but dating just didn't feel like the way to do that.

Another missed opportunity, I thought. Two days later, I found two emails waiting for me on OKCupid (in my profile, I say that I'm looking for a partner-in-crime and that I'm not averse to getting into a little trouble now and again):

Date: Feb. 22, 2010
Subject: trouble maker

hey, so i'm down for a bit of trouble now and again. well, not robbing 7-11's or anything like that but at least so good natured fun. you seem fun and cute and love music- all awesome things.

i hope you're enjoying this gorgeous sunny day before the rain returns.

A great first email, right? Followed by:

Date: Feb. 23, 2010 – 11:31am
Subject: so n.

I swear i am not stalking you! but i serendipitously happened to go out last night with some friends and there you were up on the stage! sounding awesome if i do say so.

we spoke briefly afterwards when i bought a cd and you commented on my glasses. I'm listening to it now as i sit inside watching the rain and debating a cup of coffee.

i don't believe in fate or predestination but it is quite odd that i emailed you yesterday out of the blue then ran into you last night. of course this town is pretty small also.

anyway, perhaps you aren't creeped out and will write me back. if not, alas.

I was so excited! A second chance! And from his profile, he'd done some really interesting things in his life: filmmaking, building a cabin. There were so many things I wanted to ask about. I broke one of my cardinal rules and took a minute or two at work to write back:

Date: Feb. 24
Subject: so n.

This is kind of awesome.

I don't know that I believe in fate, but it is nice to think that (good) things happen for a (good) reason.

I'd ask you lots of questions about all the interesting things in your profile, but I feel like we've already gotten the first awkward conversation out of the way, so why not just meet up? Are you around this weekend? Maybe Saturday or Sunday afternoon?

He responded the next day, Thursday, suggesting that we wait until closer to the weekend to figure out when and where to meet up. I found that a little curious (how much closer to the weekend did we need to me?), but he did follow up with several great suggestions of places to meet: all small, interesting, and quirky.

We met up for pie on Sunday afternoon, about two hours before I had a dinner reservation with friends. I got there first, and settled down with a ginger lemonade and the New York Times. He came in, and we went up to get ourselves some pie. I noticed he was missing a tooth and wondered if it would be rude to ask how that happened.

He seemed a bit distracted, and I could detect a faint odor--like he'd been running around all day. Turns out he had. "I've been going since 6:30 a.m.," he said. He and his brother had become obsessed with soccer, and they watched a match at an Irish bar that morning.

"Oh, you're into soccer?" I said, excited to have something to contribute. I told him about this story I had been working on, in which we traced the geopolitical factors (type of government, former colonizing power, whether a country is a member of OPEC) that correlate with winning national soccer teams. It's one of my favorite stories that I've worked on. I was thrilled to find someone I could talk to about it.

My enthusiasm was met with a blank stare. He made a polite comment about the piece, then the conversation came to a halt. I asked him about something else in his profile. He answered the question, I commented on it, hoping to engage him in further conversation, and...nothing.

It was one of those maddening conversations between two genuinely interesting people that just doesn't go anywhere. We had zero chemistry. "Tant pis," I thought to myself as I walked to meet my friends for dinner. "Next!"

Postscript: X. texted me the next day to see if I'd like to hang out again. I said I had decided to take some time off from dating for a bit, and told him it was nice meeting him. Maybe I'll see him around. If I knew an earthier, artier girl, I would fix her up with him.

Editor's Note: Due to an accounting error, I goofed on the date number when I did the URL for this page.

As of 2008, San Francisco had a total population of 808,976, including 93,820 single men and 83,840 single women aged 20 to 40.

Based on the best estimates by the Department of Public Health, there are around 65,000 gay men and about 27,000 lesbians living in San Francisco. Assuming that many of them are single (remember Proposition 8?), we calculated that 36 percent of single men in this city are gay and 18 percent of single women are lesbians.

After factoring in that information, there are 60,045 single heterosexual men and 68,749 single heterosexual women in the age range we examined.

There are roughly 8,700 more single straight women in San Francisco than single straight dudes. No wonder it's so hard to find guys to date.

Also, ladies, I hear Alaska and Colorado have a lot of guys. Maybe about 8,800 of you should move there, because I don't want to have to quit my band. Just an idea.

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!

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.