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Social Situations, Fifth-Wheeling, and the Dynamics of Dating
Published by Online Dating — 02-06-2026 05:02:59 AM
Social Situations, Fifth-Wheeling, and the Dynamics of Dating
Went out to watch one of my teams today. There’s a bar nearby that the alumni association frequents as the “official” fan bar for the area. Attendance was low which had the benefit of leaving lots of seats open for the taking. I really do loathe that the first thing you have to do at one of these game-watching events is scout a seat, before you’ve made any friends or accumulated any value. It connects directly with the old “this seat’s taken” experience of being in school. Some people are fine wi...
Navigating Social Situations as a Single Guy
I sat at an empty four-chair table next to a crew of what appeared to be two couples. I had slept in, so I ordered a Manhattan and a caesar salad for my midday breakfast. (My waiter didn’t know what a Manhattan was, let alone the Canadian Club version I specified – kids these days.)
I noticed after a minute that I knew one of the guys at the next table from a previous event at this very bar, which gave me an opener into the group from whence introductions were made. I initiated a bit of chit-chat about when they were in school, when they last went to a home game, and so on, but the fish weren’t really biting. We’d high five when we scored, but I would bring up topics of conversation and get one- to two-sentence answers without followup.
I noticed an engagement ring on one of the girls and asked when they were getting married. She said next year, and then started showing dress pictures on her phone to the rest of them (but not me).
I asked if they had any plans for Halloween. A dude shook his head without conviction.
I replied with mock disappointment: “don’t tell me you’re not going trick or treating!”
[Sheepish half-smile] “Eh, we’re not going trick or treating.”
They seemed like nice enough people, so I chalked it up to having all their social energy committed to each other. Fifth-wheeling onto a set of two couples who are friends already is a tough job. I sat in silence much of the day, with the anxiety tape running in my head of why I didn’t have anything good to say and how am I ever going to get back on the horse. In the end it was the situation, not me, but it didn’t make me feel much better – especially after last night’s underwhelming Halloween p...
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The Struggles of Fifth-Wheeling
As an aside, one of the interesting things about getting into a relationship as a guy is that it opens your social life to include other couples. All those dudes you never saw again because they got a wife or a girlfriend all of a sudden are open to hanging out, because you can both bring your girls and let them have a coffee klatsch while you and your bro grill or talk about weightlifting. Especially above the age of 25, there’s a steady distillation of young adults into the single and non-single ...
Thinking back on my working life, the couples I’ve become friends with usually started as work friends, and then I met their partners. Since I’ve become single, I’ve found it’s much harder to socialize with my coupled friends.
Dating Dynamics: From Friendships to Couplehood
I left the bar when the game was over, getting friendly enthusiastic goodbyes from my laconic pals. Not wanting to return to my uninhabited abode just yet, I stopped into the bagel shop for a snack hoping to hone a bit of day game. In line ahead of me were an old man paying, and a slender twentysomething blonde woman ordering. She had on well-fit jeans, low-cut shoes and a zipped-up black windbreaker. She was on the phone asking someone if they wanted anything. I noticed a modest engagement ring and ...
It’s been getting colder and rainier lately, so as she hung up I remarked on her lack of preparation. “You’re the only woman I’ve seen today who’s not wearing galoshes.”
“Ha, yeah I really should be wearing them. I’m from the north, so I really don’t think of this weather as cold.”
“Really…by north do you mean like Boston or like Canada?”
“I’m from Boston.”
How Conversations Can Change After Meeting New People
“Reeeeeally, I’ve spent some time up there myself. Where are you from?”
“I’m from the South Shore, near Cape Cod.”
“Funny, I had a job in one of the towns down there. Do you like the Pats?” (The New England Patriots’ headquarters and stadium are in Foxborough, in southern Massachusetts near the Rhode Island border.)
[With disbelief] “Of course! I love all the teams.”
“All the blue-collar guys I worked with were huge Pats fans, even bigger than the regular Bostonians. Even when they sucked.”
“They all sucked when I was growing up, and they got good when I left. So now my parents tell me not to come home.”
“Haha…thanks Mom!”
She paid and left, and I followed up with the same. I was enthused by her complete lack of sour or snarl. I gave her the opportunity to have an existentially meaningless two-minute conversation while we waited for our bagels to get shmeared, and she took it for what it was worth. After the buttoned-up experience at the bar, it was just what I needed.
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