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Dating Diary - One Man’s Story Part 1


What’s it really like to be a single guy in the big city, looking for love? One guy shares his ups, downs, and strange encounters in our new column.

By Matt S.

ant a peek inside the life and mind of one single guy who’s out there looking for love? Then check out Happen’s new (and true) Dating Diary; last week, our female columnist made her debut, and now we present the first installment below by single guy Matt S. He’ll chronicle his love life on Happen every other week, alternating with our single gal-about-town Maggie K. Let their romantic successes (and misses) serve as a reminder that dating is nothing if not full of surprises!

Wednesday, 6 p.m.
Just made a date for Saturday night… with my ex-girlfriend, Rachel. It’s been over two years since I last saw her, and we’ve been emailing a bit recently. Which has me wondering: Did I make a mistake in letting her go? I mean, here I am now 30, dating almost compulsively in the hopes of finding someone. Make that (admit it, Matt) The One. Two years ago, New York City seemed to present too many attractive options for me to stick with Rachel, so I broke it off. Now, though, I’m so burnt out on dating,
The prospect of seeing my ex again has me wondering: Did I make a mistake in letting her go?
Rachel (or at least, my memory of her) is looking pretty good: No more trying to pick up women and getting the bogus “Sorry, I have a boyfriend” line… No more awkward blind dates devised by well-meaning friends whose only criteria are “She’s single, you’re single, you’ll like each other…” At this point, most of my buddies are married or involved in serious relationships. They say they envy me my freedom. While I wouldn’t exactly trade places with them, they seem to think I’ve got a beautiful new babe in my bed every night. Yeah, right. Maybe Rachel will be up for an “old time’s sake” fling. Probably not. But one can hope.

Saturday, 5 p.m.
Why am I so nervous? I always get excited before a date, but meeting Rachel is about more than just making an impression—it’s about impressing her with who I am now. Have I improved or (God forbid) slipped a few notches since she last saw me? Let’s see: I dress better than I did when she met me, continue to get to the gym regularly, have all (OK, most) of my hair.

My bad points: Due to layoffs at my previous magazine editor position, I’m “in between jobs” (a.k.a. unemployed) and am living in an apartment with two roommates.

This does not look good.

But still, I’m feeling pretty hot when I look in the mirror. I have a few things going for me, looks-wise—height (I’m 6'4"), athletic build, a smile that gets a lot of compliments. I can do pretty well for myself, especially when I put some effort into what I’m wearing, and I sure did that tonight (jeans and a polo—don’t want to look like I’m trying too hard). When I get dressed up and go out, a little voice in my head says, I can pick up anyone. Tonight it’s also saying, Wait till Rachel sees me now. She’ll definitely want me back.

Sunday, 1:00 a.m.
Just got back from my date with Rachel. She looked good—the same dark hair and eyes, curvy figure, and cute smirk. Seeing her reminded me how I had felt about her: attracted, warm, maybe a bit protective (I’m eight years older than she is). But unfortunately, there was no bam! moment of instant attraction. Granted, the times in my life when I have been broadsided by the bam! never ended very well. Maybe I prize that kind of instantaneous reaction too much. Maybe being comfortable with someone like Rachel is what love is about.

All this was spinning around in my head as I leaned in to hug her hello. I even pecked her on the cheek—a friendly gesture I’d never used with her. Sure, a full-on lip lock would have been a good start to the evening, but after all, it’s been two years since we’ve seen each other, and the last thing I wanted to do was something rash (albeit romantic) that might make the rest of the evening really awkward if she wasn’t feeling it. And honestly, I wasn’t sure if I was feeling it, either.

Anyway, we chatted easily over dinner. Mostly we played catch-up—me updating her on friends of mine she’d met when we were together, her telling me about law school and her summer job. But the conversation did come around to “us,” the breakup, and how both of us are single again. She surprised me with the news that she had, in fact, been in another long-term relationship, and had even been proposed to. I was momentarily (and irrationally) jealous when she told me, but this feeling was quickly replaced by sympathy as she explained that she’d said no. OK, so there’s some small, unattractive part of me that’s gratified — of course he couldn’t compare to me — but I meant it when I said, “I’m sorry it didn’t work out.”

In an effort to be honest and open with Rachel, I told her I’d been dating, too—I didn’t
I couldn’t pin our easy rapport on chemistry.
want to hold back, thinking that we could only truly establish a friendship if we were frank with each other, even about seeing other people. What I didn’t mention was that I wasn’t seeing just one girl, but two, with plans to meet two more in the next week—one a setup, the other someone I’d met online. One woman, Sarah, is an attractive, bubbly Texan I’ve been particularly excited about: We’d been seeing each other once or twice a week for about a month, and I’d cooked dinner for her on our last date. But a week I’d spent out of town followed by a weeklong trip of hers had stunted the relationship’s growth considerably. Though we played a bit of email — and phone-tag, I hadn’t seen her for three weeks — and my last email to her had gone unanswered. Was she truly busy or blowing me off? And why is it always on a guy’s shoulders to do all the initiating?

It was never like that with me and Rachel. With us, it was always easy. Case in point: There we were, sitting at the dinner table for four hours total, lingering long after our plates were cleared and we’d both had coffee, talking non-stop…

Still, even after Rachel and I had shared a kiss goodnight on the cheek and the promise to “do it again soon” when we parted, I couldn’t pin our easy rapport on chemistry. Maybe it was just familiarity. And friendship. Though, I really seem to be racking up female friends that I’m not hooking up with. What’s up with that?

Sunday, 12:25 p.m.
Just called Sarah and left another voicemail—the second unreturned message and following up on an email I sent her earlier in the week. OK, I’m beginning to get the hint. And I’m not about to be one of those guys who calls and emails until he hears a definite answer—that’s creepy. Still, her behavior baffles me: What had happened? Did she not like my cooking? Did our respective stints out of town really change how she felt? Had she met someone new she liked better? That’s perhaps what bugs me most about dating in New York: It’s such a single’s smorgasbord, people can stop seeing someone without so much as a goodbye. It’s disappointing, but I cheer myself up knowing I have three other prospects lined up for this week. I’m sure something will pan out.

Sunday, 9 p.m.
Looks like I spoke too soon. Not only did Sarah not call me back, but I didn’t reach Jenny, a young social worker I’d been emailing with but have yet to speak to, either. And the other two women were out of town. How many prospects does a guy have to juggle to guarantee he’ll have a date on a Sunday afternoon?

Just checked my email and I have a message from Laura, a girl I’d gone out with a few times. We’d even kissed goodnight during our last date together about a week ago. Unfortunately, I was just not that into her and had pretty much moved on to other prospects. The subject is "Hey, this is important." I’m thinking this can’t be good…


Matt S. is a 30-year-old magazine writer and editor in New York City. His search for The One will be chronicled on Happen every two weeks.

Click here to read the next installment. Click here to read our gal writer's diary.


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