2015-The Year of Dating

The giddy songster Bruce Springsteen once sang, “When it comes to luck, you make your own” but I doubt he ever went three and a half years between relationships while in his mid-thirties, while everyone else you know is seemingly in love and married and popping out babies and definitely not going to die alone and get eatin’ by his cat.

Yes, this decided lonely state was the state I’d found myself in the recently deceased year of 2015, and it wasn’t so pretty. The concept of luck-of getting lucky, of making your own luck-seemed laughable. I’d been bobbing along on a couple dating websites (OkCupid, Match.com), I’d been set up by friends and family, I’d randomly encountered some ladies at local watering holes. But actually finding somebody to be in a long term relationship with had started to feel like quicksand-the more I writhed and struggled to find a new somebody, the faster I felt like I was sinking. I started to wonder if women could somehow sense loneliness radiating off me no matter how devil may care I tried to come off, no matter how chill and goofy I tried to play it.

I’ll be honest-I also wondered if deep down I’d stopped truly caring about finding someone else, if my relationship antennae, which had guided me more or less reliably since I was seventeen, through a constant stream of cozy long term relationships, had finally gone down beyond repair. I loved watching TV at home too much, I loved drinking alone too much, I loved being crotchety too much. Way back in college, I’d told my girlfriend at the time I was worried about turning into Ebeneezer Scrooge someday and she’d kindly replied that was impossible, but I’ve continued to harbor my suspicions. Now and again I feel a vague, self-annihilating urge rise up in my heart, something I believe is tied to my mother’s death fifteen years ago and the fact that I’m still alive.

One event from this past year stands out, dating and morale-wise. One summer night I randomly met a cute woman at the bar and we hit it off instantly-she got my stupid jokes! she was good at drinking!-and we drank for a good three hours together, helped along by my wiling wing-man Mark. At the end of the night, long after Mark had departed, I announced I needed to go home and this woman followed me out to the parking lot, the most neon of neon signs that she was interested in me, but at the last moment I panicked and said a hurried goodbye, having seen a flash of metal on her hand and telling myself it was a wedding ring which in retrospect was totally not (and I could have just asked about it, right? The stupefying perils of booze, gentlemen!). I didn’t get her phone number, I didn’t tell her my last name or learn hers. There was a moment of disbelief where she stared at me (not doubt thinking, “Really? REALLY DUDE? YOU JUST CHATTED ME UP FOR THREE HOURS!!!”) and then walked in a stunned way to her car. I stood there, watching her tight booty walk away, and felt a brief, smug feeling of having turned down a pretty girl, which was soon replaced by a wave of self-loathing at my own cowardice and asshole-ness. To quote Red Foreman from That 70’s Show, “You’re too proud? And what to you have to be so PROUD OF?!” I spent the next day sitting at my job staring at nothing, feeling a particularly virulent strain of self-loathing. I would die alone. All hope was surely lost. I spent the next week haunting that same bar, hoping she would magically reappear, but life is not a movie and I never saw her again. It got so bad I even went to the library and tried to get the librarian to give me her phone number based on the library book I’d seen her reading at the bar. Oof.

I went on something like twenty first dates in 2015. Before this year, I’d been on maybe ten in my whole life. These dates covered a vast spectrum of confusion and disappointment (I’m sure often on both ends) and each one left me exhausted. These twenty dates led to about five second dates and perhaps two third dates. No fourth dates, definitely no sex. I don’t know who these people on TV who have sex on first dates are but they do not seem to exist in my reality. Some dates fizzled within thirty seconds only to drag on for hours. Some dates seemed to go well but resulted in silence. Some dates left me paralyzed with indecision. Some dates baffled my comprehension of humanity and I could not understand why the other party agreed to the date in the first place. I dated women ranging from forty to twenty-three. A variety of body types, including one tall gum snapping redhead who wore a leather jacket I liked. I also seemed to appeal to ladies engaged in some way in the legal profession, including a well-known criminal defense attorney. These dates occurred mostly in coffee shops around St. Paul and Mpls though I tried several other activities, like going to the landscape arboretum or bowling. In the aftermath of each date, I sifted through the ash, looking for signs, for lessons learned.

Some hard-earned lessons I came upon:

Nobody is at their best on a first date. They are nervous and this makes them a little uptight. This makes them (and you) say weird shit. One person mentions they like coffee and the other suddenly announces they’ve been to South America. The earnest dater is well-advised to cut the other person a little slack because they might not really shine until that second or fifth date.

Coffee shop dates, while not exactly exciting, are generally the best way to make first contact. They’re cheap and either party can withdraw painlessly after a relatively short period of time. Though I had a couple of these last over three hours and go nowhere.

Makes sure you put important deal-breakers on your dating profile. If you’re allergic to cats, or you only want to date a fellow vegetarian, or you’re baby hungry, save everybody the trouble and state this shit up front.

Physical attraction is an undeniable factor in dating. You can go in with a general sense of what a person appears to look like but until you sit down them for a while and absorb their presence you really won’t know what’s up. I went on several dates with women who were very pretty and cool but simply did not light my switchboard-to daters out there who don’t get that follow up text or call I’d like to say it’s not necessarily (or usually) that you’re not attractive. Human attraction is a baffling mystery.

Weight loss is not everything, though it does make you feel healthier. I lost fifty pounds in mid-2014 and thought it would lead to instant dates and success. Instead a full year and a half passed before I got to debut skinnier Dave in the old bedroom.

Be kind. Everybody you’re going out with, especially in their 30s or older, has gone through some dark water themselves.

Gentlemen, every goddamn woman likes it if you open a door for them. They like small displays of kindness and generosity. You don’t have to buy a fancy dinner and act like a big swinging dick-you just need to act like a raised right man. Somebody who’d they want holding their hand at a difficult hour.

Finally, most importantly, just be yourself. The woman I’m in a relationship now, as of very recently, agreed to go out with me because we both liked to play chess. We both really, really like chess. I wooed her over several chess meetups we agreed weren’t dates and this allowed our relationship to evolve in a less job interview type way. Her name is Jen and she’s really great. We seem to fit each other, which is really the ultimate goal in all this dating effort.

So who would have thought? The answer was in the last place I’d ever expect: my own brain! Life can surprise you. Just don’t give up on it.





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