By Jake, Glamour magazine
Jake's got a crush! Listen in on his diary of the male mind in date mode, from the neurotic planning stages to the steamy good night.
I'd just broken one of my own rules and asked a woman out over email-but she said yes, so who cares? J. and I had met through friends. She'd always had a boyfriend, and I'd always wished she didn't, so when I heard she was single, I emailed her, and we made plans to see each other later that week, when she'd be, as she put it, "free to really go out."
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But, wait, what did that mean? Did she expect me to provide a crazy good time and take her to a glamorous rooftop party like the ones in the vodka commercials? Did she picture me wearing a tie and knowing how to order caviar? Should I arrange for what I think she might like, or do what I want, or some combination of both?
First Issue: The Plan
I started by running through my date options. There was the hang date, when you grab a beer and shoot pool and watch the game, just to see if she can relax and have fun. I also considered the alterna-date: a walk through a hipster-y neighborhood, a visit to a flea market or a gallery tour; guys throw this out when they want you to know they're sensitive, thinking, artsy-not your average dude. I toyed with choosing the impress-her date: expensive meal and tough-to-get theater or concert tickets. Men offer these up when we think our window to snag you is limited and we want to, well, impress. And then there's the adventure date: a climbing wall, a hidden-gem restaurant in an obscure neighborhood-both of which are a guy's way of telling you, "I'm like Anthony Bourdain: an insider, an explorer, never a dull moment. But you're safe with me." Of course, there's also the drinking date, a twentysomething's go-to. Reject! When you're getting to know someone, booze is the enemy of information retention. ("You survived a shark attack?! Oh, you already told me that? Sorry.") I wasn't sure what date I'd choose, but I knew I wouldn't choose that.
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Next Up: Prep Work
I considered what I knew about J. so I could talk about topics she cared about-her job, politics, J.J. Abrams' shows-and avoid the subject I know best: me. The guy who blathers on about his life and doesn't ask thoughtful-or any-questions (or listen to the answers) is an arrogant blowhard or insecure or both, and I prefer not to come across as either.
Finally, I took a look in my closet. (Yes, guys, too, sweat their outfits sometimes.) I didn't want to dress like a slob and make her think I didn't care enough to try. But I also didn't want to try too hard and spend all night fidgeting with my tie. The sweet spot was somewhere between the T-shirt and the suit, but where?
At Last: Date Night
I decided to swing for the fences and do the impressive-date thing, because J. is a cool, beautiful girl who I figured wouldn't stay single for long. I scored us two seats to see War Horse, the hottest play in town, and booked a table at a great Italian place nearby. I wore a jacket, a checked shirt and no tie. The conversation flowed: We joked about our nerdy high school selves, debated which was the best Arcade Fire album and lingered over desserts. After dinner we met my friends at a busy bar and drank and laughed until the DJ stopped playing. Our good night was great: a sweet kiss. Her cab pulled away and left me on the sidewalk imagining the possibilities.
The next day, I got a text from J. "Thx for the great night. U made me laugh so hard." And it dawned on me: The restaurant, the tickets, what I wore-none of it mattered. In the end, the only thing that mattered was that I'd made her laugh.
What does this mean for you? Well, if you spend all your time trying to decode the first-date choices of the guy you're with, you may miss all the fun. If he meets you at a bar wearing a hoodie and cords, it may mean he doesn't care, or it may mean he feels really comfortable with you…or it may just mean he needs to do laundry. J. didn't read into things too much, and that produced two emotions in me: happiness and worry. Happiness, because I think I may have met my dream girl. Worry, because, well, what do I do for an encore?
Jake is a real, live single guy dating in New York City.
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Photo Credit: Condé Nast Digital Studio