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It's late Friday night, and the bar in which I find myself is like an ancient ship's lower deck: dark wood and barrels. The band performing in the far corner matches the mood. It's a jug band, which is exactly what it sounds like: a few guys drawing bassy notes out of empty jugs while another guy plays a guitar made out of a cigar box. Couples are dancing, drinks sloshing out in little waves. I'm out with my close group of friends and, of course, I see a very attractive woman getting a drink at the bar. First I see her in profile, her dark hair tucked behind her ear. But when she turns to look out over the crowd, I see her brown eyes and bright warm smile. And she sees me. She's pretty to the point of intimidation, but, importantly, I do not look away. And she doesn't either.

We have a nice long moment.

Walking over to the bar, with the hope of introducing myself to her, it occurs to me: What exactly am I looking for in this woman? What am I hoping to find? I'm past 30, almost settled professionally, and I feel like it's been far too long since I've met someone I could fall in love with. I'm not sure if any of us can recognize real, lasting love the first time we meet somebody, but there a few things that help a man decide if a first meeting needs to turn into a first date.

1. Assume Your Awesomeness

Though it can be difficult (trust me, I understand), assume you are an awesome, quality person. This is not about having a big ego. It's about not feeling insecure, not laughing too often and too long at what is not funny enough and not agreeing too fast and repeatedly before any actual points or ideas are fully expressed. Because when you're busy thinking about all your possible flaws and faults, you might end up sounding like this: "Yeah, totally, haha, yeah, haha, totally, yeah. Haha." If you take your awesomeness as a given, you can focus on finding out what is awesome about the guy you just met. This will ensure you remain genuine, and the conversation will end up the same way. That's something I highly respect in a woman. Haha, yeah, totally, yeah. Haha. For serious, though.

2. Skip the Sharp-Edged Wit

Every online profile, every random dater, every TV single person all say they want the same thing in a mate: a sense of humor. From men and women. But the pressure to be funny, when mixed with a healthy dose of nerves, means that conversations easily veer into banter. But banter often flips directly into sarcasm and making jokes at your date's expense. What ever happened to sincerity? Sincerity is wonderful. Sincerity is milk chocolate; sarcasm is a grapefruit. In the past, I was deeply in love with a woman who never tried to make jokes. Not that she never laughed (I still miss her laugh), but she just didn't feel the need to be constantly funny. And neither did I. Love doesn't always need a laugh track.


3. Arrive Mentally Unaccompanied

I'll admit it. During encounters past, I had the habit of mentally inviting along some of my friends, who took a seat on the discussion panel, right there in my head. These were friends who would disqualify a woman for the way she dressed or laughed. Her job. The fact she was a vegetarian and other ridiculous criteria. Meeting somebody was like a reality talent show, and no one was going to advance to the second round, according to this absurd panel of judges.

Now I can feel it if my date has invited her friends to sit on that panel to uncover what must be wrong with me. Recently, out of nowhere, I was asked this question on a date: If I were given $1,000 right now, what would I spend it on? I knew she was testing me to see if I was cheap or if I'd spend it on her. The question made me feel really judged. All I ask is for my date—and for myself—to show up mentally unaccompanied, so we can both spend the whole night discovering what exactly we do like about each other.

4. Try to Hear the Candle Burning

Before I turned 30, I registered words and concepts, but I hadn't yet learned how to truly focus when a woman was speaking, how to stop my brain from shuffling through other thoughts like: Where should we go after dinner? Why does my right heel hurt all of a sudden? How is this date going—maybe I shouldn't have ridiculed people who are overly enthusiastic about yogurt? My mind used to whir like a power drill, boring for the next topic, and I couldn't hear anything over that metal-on-metal thought grinding. But now (and...okay...this is something I still have to remind myself to implement), if I just take a damn moment to focus...I can hear the candle burning. I can clear my mind and let it be refilled by the words of the woman I am speaking with.

As a result, I can certainly tell when the woman I'm with is herself mentally distracted. Her eyes are everywhere but on my face, and her hands are busy with her hair or the napkin on the table. But when she commits to honest-to-God listening, I can feel her eyes on my lips, the way her expression reacts softly to every word I'm saying—and that drives up the romantic tension like you would not believe.

5. Tell Me Exactly What I Want to Hear

Even with a jug band playing, there is one thing I love to hear from a woman. What one thing is that? Anything. As long as it's something she's passionate about. Her job, her art, her hobby, her rescue dog, her family, her Ford Focus (if she can pull that off). Women who know what they want in life, women who are actively trying to get it—there is nothing sexier than that, because nothing sounds more enticing coming out of a woman's mouth than something she feels passionate about. And if she is insanely passionate about what she does, then we'll understand each other, because I'm also insanely passionate about what I do. Maybe this is jumping ahead, but I'll also know that I'll be able to support her in what she's trying to achieve and she'll be able to do the same for me, which is what people with degrees call the ability to grow together. My own take is: If she's driven, she is going to inspire me. And finding a woman with the ability to inspire me is exactly what I am looking for. That, and a woman with the keys to a 2003 Ford Focus.

While the jug band takes a break, I'm still hoping to introduce myself to the dark-haired woman at the bar. But she's still speaking with her friend. That's when I realize: All of these things I'm looking for in a woman are also, invariably, things I should embody myself. Because here I am, failing to be bold, keeping my passion to myself and not even putting myself in a position to listen to her. I'm seconds from speaking yet still not sure what to say. But just as I take a breath, she's pushing her finished drink deeper into the bar, giving her friend a hug and walking out of the bar.

Later that night, my own hesitancy keeps me awake. I keep flipping my pillow, smacking it around. Maybe the woman from the bar is at home feeling the exact same way. What would I say to her if we could talk right now? Definitely this: There'll always be another chance to meet someone worth meeting. And next time, both of us will be ready.

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