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It’s tough to pinpoint when the feeling started. It was there over the summer, maybe sometime in July or even June, but I bet if I was really listening to myself, I was probably singing the tune even earlier. March, maybe February. Sort of like an eager restlessness, but a sad kind. Not depression, per se, but lingering feelings of “this is it? This is what my twenties are supposed to be like? Surely there’s more.”
But when I’d ask myself what I really wanted, I’d give myself a mental shoulder shrug, ambivalent, taking another long swig of drinkable $10 wine, the bottle always dangerously low on volume week after week after week. Though to be fair, even if I were keeping things one hunit emoji, I’d be at the bottle of a bottle of wine. But my morose wine is red, and my happy wine is white, and for a while I’ve only been drinking red – even during the dog days of summer – so you know things weren’t all blueberries and paper airplanes for Boston’s boy.
Staying busy with work was a great distraction from this feeling, but there are only so many hours in a week you can stare at PowerPoint before an ophthalmologist has to bring in the heavy artillery to remove the gloss from your corneas. So I wrote. Lost myself in satire blogs, cracking jokes about The Bachelor and brunch. So I read. I had lists of books I’d always wanted to conquer. I read some. So I travelled a little; took some nice Instagrams. So I got a shredded. Abs like Bieber. Okay that last one is a lie.
Dating was getting exceedingly more difficult. Well, more just the act of meeting people. I have this theory about Boston. It’s an incredible city – don’t get me wrong – but it can be a tough place to meet new people. My theory about this is because people who grow up here tend to stay here, or if you went to college here, lots of those people from your college crews tend to stick around. (Except my college crew; more on that later). So you’ve got a city full of groups of friends pretty solidified, and they usually roll deep. But getting “absorbed” into one of these friend groups, as an outsider of the squad, is wicked hard.
I see lots of people dating within their friend groups, or dating friends of friends. But when you’re like me, and you’ve met all the friends of friends, met all the single girls my friends know, what’s the next step? Where do you go from there? I was still meeting people, but at a much slower pace than I would like. It’s not that I’m deeply pining for a girlfriend; I’m currently content at the moment only being committed to Bill Belichick and New England Patriots. But right now, on the brink of 26, I just find myself not even being consistently in positions to even meet people who I could potentially one day fall in love with.
And like I have mentioned, I was bleeding college buddies left and right. Always close with my roommate, we got even closer. Not in the “bite that tattoo on your shoulder pull the sheets right of the corner” sense, but I spent a lot of time with him. And his girlfriend. I did a lot of third wheeling; I was the biggest third wheel since Italy in WWII.
Some friends still kicking around Boston started moving in with their girls as my friends from college were disappearing to other cities. They were all getting jobs elsewhere and leaving me to defend the wall up in Boston alone. I was losing my infrastructure of single male friends faster than an Oberlin College graduate took to the protest streets after the Presidential election. Of the friends that I had left in Boston, many were in serious relationships. Do you know what it’s like being one of the only single dudes in a group of friends mostly comprised of couples? For one thing, it makes meeting single women really hard really fast. But more than that, it can get really lonely. What the fuck was I supposed to do when they all wanted to go to fucking farmer’s markets to learn the difference between winter and summer squash.
And then one day in mid-July I came home from a trip to Nashville and The Roommate told me he was moving out. He, too, was moving in with his longtime girlfriend. Certainly happy for him, I was at an impasse. Unhappy with how my life was trending, I could stay where I was and find a new roommate and try and find ways to hang out with more like-minded single people. Or I could really shake things up.
“I’ve lived in Boston my whole life,” I told myself. “A lot of the guys from college have moved out of Boston. Maybe you should go join them. It’d be an adventure.” So there, sometime in late-July, it was decided. Boston Max was going to move.