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Dating in Your 30s

5 min read
The Bold Italic

By Caleb Garling

Illustrated by Andrew J. Nilsen

I broke up with my girlfriend, and I loved her very much. We tried so hard. For years. Left everything on the field. And it just wouldn’t work. We wanted it to. For reasons that aren’t your business, they didn’t. Sometimes, as shiny as those gears are, they just won’t turn.

So as a 30-something, I was spit back into the wilderness of singledom. My heart wasn’t broken; it was bent. I would joke darkly with friends that it would have been easier if things had ended because one of us had cheated. But it died of cancers, not a bullet — so I was left trying to fill in the blanks.

I had depended on things. I had depended on her depending on things. Assembled correctly, that balance is the elegance of a relationship.

But when I first hit the market again, the teeth of my gears were spinning aimlessly. The obvious anecdotes came into play — habits I’d had as a roving 20-year-old resurfaced. I had pizza four meals in a row. I wore my underwear inside out to avoid laundry. Yet after a five-year hiatus, singledom had new layers.

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I realized I missed having someone know how much I love macaroni and cheese or fly-fishing. I didn’t want to explain why I’m a dog person or list the five bands I’d take on a desert island. I didn’t want to figure out what subjects are OK to joke about or how someone felt about Barack Obama.

I had trouble with the get-to-know-you questions. I had covered them for five years, but I also saw them differently. When I was in my 20s, it was a deal breaker if a girl didn’t love Led Zeppelin. Now I don’t care. But she’d better be moved by (good) music. When I was in my 20s, it was a deal breaker if a girl didn’t like camping. Now she’d better be adventurous. When I was in my 20s, it was a deal breaker if a girl didn’t read fiction, appreciate science or keep up on the news. Now I just want someone curious.

These aren’t compromises. This is a guy knowing now that dating doesn’t exist on paper (which may explain my resistance to doing it online). The formalities of asking where people grew up or where they work or their favorite color don’t help me get to know them; they just give me information about them. Who cares where we went to college? How about, what was the last thing that made you laugh until you cried?

I could quickly sniff out traits that were both familiar and safe, new and unfulfilled. I went out with girls who were put together and organized, like my ex. And I went out with girls who were off their goddamn rockers. I came back to center to a girl so sweet and thoughtful, then wandered the drafty halls of another’s self-absorption. I believed that I was operating my dating life with something that resembled intention, filling in the teeth of those gears somehow.

I was also acutely aware of myself. My typical demeanor is pretty quiet, but when you draw me out and get me going in a debate or on a topic that really interests me — music, writing, politics, the outdoors, science — I can become quite an extrovert. On a date, I’d have to keep in mind that that transformation is something people don’t immediately know about me — it’s learned — but that was tougher to remember when we were a bottle of wine deep.

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I was obviously doing a bit of running — in the figurative sense — while trying to ignore a cruel whisper that “maybe I’m not right for long-term commitment” and “maybe long-term commitment isn’t right for me.” Women do not have this particular market of angst cornered, by the way. Guys just manifest it differently.

I did irresponsible things. I did disrespectful things. I didn’t call girls back when I should have. I participated in other people’s infidelities. I partied a lot, sometimes too much. I spent eight days at Burning Man. I basically slammed on the gas, fired the engine and hoped I’d drown out the music. Not that I was a choirboy when I was in a relationship, but again, there were new layers. When I’d turn off the engine, the notes from that music continued ringing in my ears.

My buddies were getting married. Others were having babies. We were all part of the same club, but now I found myself ignoring them. “I don’t have the time,” I thought. “I’m rebuilding my own life.” While in a secret corner, I was thinking, “That should be me.” Weakness masking as determination.

The doubts became louder with every “So…you dating anyone?” from my family. Harmless question. Full of genuine love. But trapped by the inescapable gravity of “We’d love to see you married.”

Then that angst reached concert-level crescendos during those in-between moments that make love and partnership so rich. Like when I’d wake up Sunday mornings and drink coffee by myself, or be unable to find anyone to drive to Marin with. Loneliness hits hardest when it is not a choice. And it manifests in weird ways. I realized I wore my sunglasses on BART a lot.

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But an important gift finally came home to roost: music. I formed a band. I started singing. For my first time in 15 years of playing, I wrote complete songs — quite a few, actually. I picked up the mandolin. And the ukulele. I would ache to get into Dolores Park and jam with my brother. My guitar became my refuge, where I did my best thinking, where I released the tensions and gave emotional tangibility a face.

I poured myself into songwriting, and when I’d finished, I heard the song “Gagging Order” and realized that’s all I was trying to say.

“Move along / There’s nothing left to see.”

I hadn’t accepted that.

My old life was over. I wasn’t going to find a replacement for it no matter how much I tried to build a composite out of my new one. I needed to clear myself of it. Not know that it was done but understand and feel it. And after enough hours alone and in my band’s studio with my guitar, after enough coffee and drives to Marin by myself, and after enough long and rich conversations over beers with my friends and brothers, I did.

When I became single again, I hadn’t been dropped on the ground; I’d been catapulted into the air. Now my feet were on solid earth again. I forgot the crap about marriage and the rest of those silly pressures. So what if I was a single 30-something? You can’t do anything about the social whispers other than live your life. I’ve moved along now, excited by what I see.

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Last Update: September 06, 2022

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The Bold Italic 2415 Articles

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