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.

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.

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.

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

Date: 7/14/09
Subject: Hiya

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

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

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

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

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

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

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

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

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

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

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

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

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. :)

I almost always find someone in my Quiver who's attractive and interesting. Reading S.'s profile, I wondered if the algorithm had created someone for me. Some highlights:

• He likes music that's poppy and twangish
• He likes talking politics and describes himself as a moderate who votes Democrat
• He loves Scrabble
• His favorite Beatle is Paul and favorite Monkee is Mickey
• He listens to Benny Goodman, Big Star, Crowded House, and all sorts of other bands I thought I only listened to
• HOWEVER, he was anti-serial comma. (For non-editors, the serial comma is the comma that comes before the "and" in a series of three or more items. Ex. peanut butter, bread, and jelly. Editors divide into two camps on the issue. Serious stuff.)

How could I not email him?

Date: 02/28/2009
Subject: I think we agree on everything but serial commas

Hey!

How can someone like all the goofy things that I do -- Scrabble, NYT crossword, twangy music, even Big Star and Benny Goodman -- and yet be averse to something that I hold so dear: the serial comma. (I have "pro-serial comma" as my religious affiliation in my Facebook profile.)

Actually, I don't know if that's a rhetorical question. How is that possible? The serial comma is at worst, harmless, and at best, helpful. My theory is that lawyers decided to abolish it so when they had their law firms' signs made, they would be one character cheaper.

He wrote back.

Date: 03/01/2009
Subject: I think we agree on everything but serial commas

Hey! My disdain for the serial comma started with the AP Stylebook and was encouraged by Vampire Weekend. Blame them. But some of my best friends (Strunk, White) are fans, and secretly I'm pleased if anyone cares enough about commas to have an opinion one way or another. (The only grammar thing that really, truly makes me blow my stack is when people stick apostrophe's in plural's for no reason. That makes me crazy.) Anyway, I don't think the comma thing should be an insurmountable obstacle.

We do seem to have an awful lot of things in common. I actually think I've seen you around -- perhaps in the Friends & Family area at Hardly Strictly?

I see Rhett Miller is playing at Yoshi's-SF soon. You going? If so, let me know and we can shake and howdy, as they say in the biz.

Gotta run. I'm supposed to play tennis with a friend at noon. Let's hope the rain holds off for a while. Thanks for writing! Ball's in your court now.

It turns out we both lived in Boston, both worked in publishing (he in newspapers, me in magazines and online), both covered music (we even knew a lot of the same publicists), both played mandolin in bluegrass bands (he only briefly). Weird.

He lives about 45 minutes south of me, so we split the distance when we met for coffee. The day we met up, I had a horrible attitude. Frustrated with Match and my resume date, which was the day before, I barely put on makeup, left a bit late, and grumbled to myself the entire half hour drive down.

But I had a great time. We had so much in common, and he was really nice to chat with. Newspaper people can be great to make small talk with. They put their interviewing skills to good use. After coffee, we walked around town a bit before hugging goodbye and pledging to hang out again.

Over the next week or so, we kept up a really nice email correspondence, then he invited me to see Throw Down Your Heart, the documentary about Bela Fleck's trip to Africa. We met up for dinner and went to see the late-ish movie.

Dinner was fun, and we had a great conversation. He asked me some really interesting questions (like, "Have you ever been married?" No. "Ever get close?"), and it was fun to actually talk about those things that you wonder about when you're getting to know someone who you might want to date.

Also, in the interest of full disclosure: I was super tired, so I may not have been as open or engaged as I could have been.

At the end of the night, I still wasn't feeling sparks. I really liked him, but I wanted him to be my friend, not my boyfriend. We were kind of too similar. Music and writing were both of our things. I know it sounds strange, but I like it when music is my thing and when the guy I'm dating has something else for his thing. I like being with someone who expands my horizons rather than consolidating them.

So I cowgirled up and emailed him (I maybe should have done it over the phone, but all our correspondence had been through email and text, so why break the pattern?). Among other friendly chattiness about music and concerts, I wrote:

I'm really enjoying hanging out with you, but I have to be honest and say that I see much more friend potential than romantic potential. I would really like to continue being friends and go see some shows together. But we did meet through a dating site, after all, so I absolutely understand if you're focused on finding someone to date right now and want to spend your energy on that.

I wanted to give him an out in case he didn't want to be friends. He wrote back, among other chattiness:

Friendship sounds nice. (Although that "much" was a bit harsh!) Thanks for being so honest and straighforward. I'll be sure to let you know when I have a +1 for a show down your way that I think you'd enjoy.

I totally didn't mean the "much"! (I wrote him back to tell him that and that I was glad he called me on it so I could clear that up!) That's what I get for hanging out with a fellow editor.

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.

I should probably elaborate on the kiss with B. It was nice. Just nice. But you need to keep the expectations low for first kisses, right? There are too many other mitigating factors -- extreme nervousness being the main one -- that can make an otherwise good kisser deliver a less-than-stellar kiss. Mediocre first kisses are not a deal-breaker for me. Chemistry can still develop.

So when B. texted me a few days later to say his friend had extra tickets to Dave Matthews and asked if I wanted to go, I thought sure. I don't love Dave Matthews, but my brother, a drummer, raves about their live shows and it sounded like a fun thing to do. Plus, I'd get to meet some of his friends. If you feel that you could hang with the guy's friends, it definitely ups the long-term potential for the relationship.

B. met me at BART, and we drove over to the show. We bought some beers, ate burgers really quickly, bought more beers, and sat down with his friends. B. barely talked to me. He leaned over me to talk shop with his friend. He barely made eye contact. It felt like second-date nerves. I didn't want to talk through the whole show, but the conversation was a bit forced. I was still feeling on the fence.

After, he gave me a ride back to the city, which was sweet. I invited him in, I offered him a glass of water, we chatted for a while, then I said I needed to get to bed. I figured, "OK, that's it. And I'm kind of fine with it." B. put on his jacket, and then he started kissing me. I was a little shocked, but it was better than the first time. At 1 in the morning, we said goodnight.

This is when my brain starts playing tricks on me. There must be some scientific study into the effect of smooching on a woman's brain. The same pattern plays out with me: I kiss someone, I like them better, I want to kiss them more. It's as if all these voices in my head are saying, "He's nice!" "He's cute!" "He's interesting!" and they drown out the voice that says, "Hey, you've hung out with this guy three times now. And yes, all those things are true. But you still are on the fence about him. Maybe it's time to move on."

Part of why I'm doing this whole thing is to listen to that voice more. Because that's the voice that says, "He is a great guy -- for someone else. And you are a great girl for someone else. Stop wasting each other's time." Relationships begin and end every day, and it's not about the individuals, it's about the fit. I was overruling the part of my brain that said, "B. isn't the best fit for you." I continued to overrule it.

Afterward, we all had another drink at the bar. I walked back over to the group while B. was in the middle of revealing a plan. "We're going to the Serenader, you in?" he said to me, with a glint in his eye. "They have a great band crammed onto this tiny dancefloor and they play everything from jazz to blues to funk. It's great."

The place was tiny but hopping: people talking, coming in and out, and everyone dressed to the nines. There was one lady in a skin-tight snakeskin-print jumpsuit. Another guy, just inside the door, was in a full suit and hat, looking like he stepped out of the 1950s. An older gent was wearing a full military uniform. The sign outside said that the club is 21 and over, but since this is a mature club, they prefer 25 and older.

B. went in first, and put his hands up to get patted down by the security guy, a big dude who could look imposing when he wanted to and had a pencil-thin goatee tracing his jawline. He found something in B.'s pocket. "Is that a pistol?" he said. B. nodded. "I'm a cop," he said, pulling out his ID. The security guy looked sideways at him. "A cop?" he asked. "I won't tell anyone if you don't," B. assured him. The guy let him in. "I'm going to have to see inside your purse," the security guy said to me. I unzipped it halfway, and then he caught himself, "What am I saying? I just let him in and he has a pistol! Go ahead." R. made it through without incident.

The postage-stamp-sized parquet dance floor was filled with people dancing to the recorded R&B playing over the sound system. "There's no band!" B. said, clearly disappointed. Feeling flush with my gig cash, I offered to get the first round and moseyed up to the bar. The bartender was a tall guy with super curly hair, who was on top of everything: without acknowledging anyone, you could tell he knew exactly when each person got up to the bar, and served them all in order.

It was already late, and I was feeling a bit fuzzy-headed from the couple of beers I'd had on the gig. "I'll have a Capt. Morgan's on the rocks [for R.], a Maker's and diet [for B.], and a Corona [for me]," I said. "We're out of Corona, we have Miller and Bud," the bartender told me, setting up the glasses for the other two drinks. "I'll have a gin and tonic," I said. "We're out of tonic." "How about a gimlet?" Done.

The bartender made all the drinks fast -- and with pretty generous pours. So much for taking it easy. R.'s rum on the rocks came in a wine glass.

The music stopped briefly and "Signed, Sealed, Delivered" came on, sung by a woman. There was a band! We made our way through the small crowd and staked our claim on a spot just off the dancefloor. There were three vocalists, one of whom also played horns, another horn player, drums, 5-string bass (played by an older guy who looked like he was born to wear hats), guitar (played by the only other white person there), and keys. The female vocalist was tiny, but man, she could sing.

B. pulled me over so we could get a better view of the band. "Two opposite ends of the musical spectrum," he commented -- bluegrass to Bobby Brown. At 1:15, they called last call and started shooing people out the door the minute the band stopped. I heard the manager tell the band, "Anything that's not out of here by 2:30 gets put out on the street." They run a tight ship over there.

I put down my half-finished gimlet, and we watched people file out the door then filed out ourselves. B., R., and I chatted for a bit on the street, then B. walked me to my car (parked directly behind his), and leaned in for the kiss.

Now let me digress for a moment. First kisses are always weird -- it's the first truly intimate moment between two people who, often, don't really know each other that well yet.

It's my theory that the weirdest part of the first kiss is the seemingly interminable time span when the guy (or girl) starts leaning in and the only thing you can look at is the kiss initiator's face -- which, let's be frank, usually has a ridiculous expression. It can't be helped -- there are too many other things to think about at that moment, and controlling your facial expression is really quite a minor point. But it does lend a feeling of absurdity to the whole thing.

That's why first kisses between a short girl (such as myself) and a tall guy (such as B.) are particularly weird. The guy has a much greater distance to travel. It's just geometry. But that means that you have more time to look at his expression. And that means that the short person needs to make sure she doesn't get the giggles.

So he kissed me. I didn't get the giggles. And it was nice. He showed me which way to go to get back on the highway, said goodnight, and told me, "Drive fast and reckless!" And when I got home, I saw I had a text from him asking if I made it home OK. Fun AND thoughtful. I love it.