I hadn’t noticed him when he and his friend walked into Waterfront Bar in Little Italy. When Ryan (not his real name) came up and began introducing himself, I didn’t think much of it.
And then, I looked up. Six-foot-three, wearing a flat-brimmed hat and large grin—my five-one self was suddenly glad that I became a rock climber during the pandemic. Within minutes we were chatting and flirting. His hand began to graze my lower back as he spoke.
And then we kissed.
Smooching in bars at 40 isn’t my idea of romance, but if you make it to the top of the Empire State Building, you don’t miss out on the view.
At the other end of the bar, in a fun twist, my ex John was shooting his own shot with multiple women. There are some days that seem more scripted than others. Maybe I really am living in a rom com—or at least a comedy. Most days the rom feels elusive.
Ryan got my number and texted me the next day, but I didn’t hear from him again until three days later, when I reached out. The Lion’s Share in downtown was throwing an anniversary party, so I asked him to be my plus-one.
He was wishy-washy about his answer up until the event started. He agreed to show up a little late. This was the first time something inside me wondered if he was the commitment type, but it was still early.
I got butterflies when he arrived. He was immediately affectionate, stroking my back and complimenting my outfit. We kissed on barstools in a dark corner later that night as we sipped on tequila sodas and beer.
As we chatted over the next couple of days, I let him know that I didn’t want to be the only one asking the other person to hang, but still, I invited him to watch the Super Bowl with my friends and me. He said he’d let me know.
When he didn’t show and instead asked if I wanted to come by afterwards, I declined, feeling that sense women get when a guy only asks to hang late at night.
A few weeks after meeting Ryan, my matchmaker set up my first date with a pre-vetted person: Connor. He’s 44. A lawyer. He goes to therapy. He’s active and an avid traveler. He wants a family and loves pupusas (the food of my Salvadorian roots).
On paper he seemed like a catch.
My matchmaker let me know we’d be meeting at Stone Brewing in Liberty Station and gave me his number the day-of. First dates are always a little nerve-wracking, but meeting a complete stranger (save for three mediocre photos and a quick bio) was a bit less intimidating.
When he walked up, my initial reaction was that he was attractive, though not exactly my type. But Connor surprised me. I didn’t feel the same butterflies as I did with Ryan and we didn’t have the same flirtatious banter, but we had more meaningful conversations.
Connor showed up as a man—meaning, he didn’t seem like many of the young guys I had dated before. He spoke with self-awareness, shared his points of view while listening to mine, and asked me enough questions that I felt like it was a conversation and not a one-sided interview.
We also shared personal family stories. I opened up about private things that I would never share on a first date—stuff I’d usually withhold until we’re closer to relationship status. He told me about his family dynamics. Conversations like this could be uncomfortable for some this early on, but I appreciated that he laid it out for me and allowed me to decide what to do with it. There was no hiding for either of us.
After the date ended, he walked me to my car, we hugged, and I went home. I don’t think my insides were doing somersaults, but I do think meeting someone who has worked on themselves, knows their value, and possesses emotional intelligence is becoming harder to find these days—at least in my own dating life. It was refreshing.
He texted me before we went to bed, thanking me for hanging out. He also brought up an awkward moment that had occurred during the date and addressed it so that it didn’t linger longer than that evening.
Connor asked me to hang out again. Our next date is planned for tonight. He picked two places ahead of time—neither is in our neighborhoods (he had to do his research). It’s this little bit of effort that, in my convos with others, really makes a difference nowadays.
If I’m being honest, though, my gut is sending up a few warning signs with Ryan while my emotions need to catch up to my brain with Connor. I’m used to the Ryans of the world and see glimpses of my ex in him already. It’s easy to dive in head-first when the attraction is front and center, but I know that I don’t want to do the heavy-lifting while I date anymore.
With Connor, I’d normally be quick to assume it’s not a match. Not because we didn’t have a lot in common, but because the immediate attraction was missing. It’s not a novel concept to me that you can fall for someone’s character before falling for their looks. Some of my exes started as friends. But it’s sincerely hard to always put it into practice—especially when you feel like time isn’t on your side anymore (hello, 40).
Part of writing this column is to take accountability for how I date, but to also be willing to make the kinds of decisions that can finally change the course of my previous love stories. So with that, will I be able to cut things off with Ryan if he can’t match my dating efforts? Can I give Connor the time needed for something more to develop?
Time will tell how each plays out, so I guess you’ll have to come back next week to see how things are going. I’m curious to find out myself.
If you’re new to Unhinged, catch up on all the dating chats you’ve missed here and follow along at @monicles and @sandiegomag on Instagram to know when a new article drops each week.
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