If you think you can handle how this is going to end, then go for it

Jim and I met on a dating app mid–way through 2021 and after I had recovered from COVID and hospitalization. I was eager to date and resume my normal life of dressing to impress and drinking like a fish (but secretly feeling self-conscious - I also think Secretly Feeling Self Conscious should be the name of a unisex fragrance). One swipe on a balmy and beachy August day in Myrtle Beach, SC - because you know I was scrolling and trolling from South Carolina so I could line up a date when I got back to NY feeling more confident. Why more confident, you might wonder? Because tanned skin is toned skin. Moments later, a match. Our messages were exchanged with rapid fire humor and we broached intensely important topics of value such as tanning, growing up Italian, bread, cocktails and cooking. I was smitten, clearly. There were red flags a plenty from the fast paced messages and an offer to pick me up from the airport as I waited to get on my flight back to NY. A barrage of messages and his taxi offer were ambitious and well played to get laid, but I wasn’t having it. I would decline the ride because as much as I wanted to meet him I wasn’t meet-up ready in my overalls and with my beach hair. 

The next day a date was immediately set to meet. He offered to come to my neighborhood, chivalrous and also suspect. I was clocking, but I didn’t care. He had gray hair, glasses, a photo with a dog and met me on my base level of bronzed skin. We had a bet about who would have the better tan. My type of guy, my type of trouble, but he’d only ever see me in a bathing suit or naked - drunk - you better believe it.   

Our first date led to making out in his car after I found out he was only just 3 months separated and still going through a divorce which would take at least a year to finalize. He smelled good and paid for drinks. Did I mention he had a dog, part-time?  I was willing to look past the divorce paperwork. And, though he read “Fun guy alert,” again, I ignored it because “I’m fun, I like fun! And I’m casual, I can do casual.”

Much like the track record with most of my dating life, I was going with the flow and lying to myself. I was trying on, on average, 4 outfits before I left the house and wondered “Will he be attatrected to me?” Never once thinking, “Will I like him?” A second date turned into a complete backing off “I’m not ready to date anyone seriously,” he said. My response, “We’ve seen one another twice, we’re getting to know eachother.”  That was true, but another red flag. It wasn’t that he was not ready to date anyone seriously, it was that he didn’t want to date me seriously. We took a ride to his house in the Hamptons and bought wine on the way. We spent the day drinking, playing records and went to a dinner on the water. I slept as he drove home and woke up in front of my apartment. We kissed, but we’re not dating. I went along with it. There was pull back and restraint, I dated a few other men while he and I kept in touch - but I knew it was going nowhere. Yet, I reached out. I asked how he was. I did my usual dance with kind texts and care, all while knowing in the back of my mind that he would likely never change his mind. But I was a seeker of mindchanging and validation, I didn’t know how to stop myself. I didn’t know how to stop myself from trying to be liked. 

I put an offer on a small house in Beacon, NY - time passed quickly between texts and seeing one another in person. He called, while I was there, and I invited him to come visit while I was away for 3 weeks - which was met with a “maybe.” But he called. We talked more than normal, deeper and about family, money and life choice. He opened up about his own insecurities. I thought “maybe this is something if he’s opening up, maybe this is something if I feel like I can open up.” While I was away I bought him cufflinks at a weekend antique fair, they were perfect and reminded me of him. I told myself “We’re not dating, but we talk enough, I think it would be nice to get him a birthday gift.” I texted him for his birthday, a reply that he was having a party in the Hamptons. Really, who was I kidding? I was not Hamptons. I didn’t even want to be. But I told myself “You know, people from different sides of the tracks get together all the time, don’t be so quick to judge.” 

We went to dinner together right before Thanksgiving. Between trying to buy a house, the offer not being accepted, purchasing cufflinks and accepting his dinner invite - I also cut my hair. Cutting my hair is a typical Tina tell tale sign of sadness and wanting to manage change when I knew something else had to give. I met him, with my bangs, a thrifted cocoon sweater, cream leopard print pants, a black bodysuit and loafers. I felt different and confident. Well, for me. But I was brooding in anxiety. He seemed touched by the cufflink offer and I wanted to pay for dinner but he wouldn’t let me. We hopped from bar to bar in my neighborhood, sharing non-commital cocktails and nothing about us was linked or cuffed. We had more fun. I continued to tell myself this was ok. 

Christmas rolled around and the New Year. I was also dating someone who was about as entertaining as watching paint dry. I dated an alcoholic who couldn’t get it together to show up to work or our dates on time. Jim’s texts came through, once a month for a night of fun and I continued to accept. 

We met at our usual spot. A bar where the cocktails were nothing short of perfection and the bartenders entertained by mine and Jim’s comical banter. We appeared like a couple in our once a month dress-up to go to the bar we always went to. The bar where we had our first date; where he would always pay and where everyone knew our names. Where I imagined I could be someone’s girlfriend for the first time in my life. 

When he asked me, finally, “Are you seeing anyone else?” 

“A few guys, but no one I’m particularly interested in,” I said. 

“Oh, ok.”

“What about you?”

“No, no one special.”

“Ok, cool.”

He drove me home three blocks to my apartment. We kissed and he told me “If we F#$K I’ll never talk to you again.” I was drunk, my dress was down and I had no idea what that meant. I pulled the top of my dress up and he walked me to my front door. Another month rolled around and our in person dates turned to FaceTimes with wine and banter. A screen to block emotions, physical intimacy and any desire I had that this might ever be something. We were 6 months into knowing one another when he told me on FaceTime that a coworker suddenly passed away. He was supposed to go to his Hamptons house the next morning to work on a few things, but when I texted him he said he didn’t go.

“Do you want to come over and hangout?”

I said yes. I said yes knowing what he said when we met “I don’t want to date anyone.” and “If I f$%k you, I’ll never talk to you again.”

I went. I took the MetroNorth in the dead of a NY February in 2022, one week after quitting my job. I baked cookies and I went. I went because he opened up and because even if I knew something would never happen; something was better than nothing. His dog was there, big, white, shedding and sloppy - but cute. Cute and old, like his owner. I rubbed his belly, the dog, while Jim made cocktails and I took in his home, its energy, his stuff. Mainly thrifted, well curated, a record collection larger than the one in the Hamptons. A lot of beige and understated artwork that leaned on walls and waited on the floor. A man's apartment with the essence of a woman remaining, he lived there with his wife when they were together. He had just picked the dog up from seeing his wife, so I asked no questions. We were not anything. Unnamed. But I was there. He wore a white button down shirt and dark blue jeans, loafers and looked neat. Me in my black bodysuit, jeans, cardigan and converse. That morning of selecting an outfit to wear knowing I had to take two trains to MetroNorth and had a 75 minute ride ahead, with a chance of snow, was a disaster. A tornado of clothing carnage tossed in my bedroom. I called him the entertainer. I did nothing but request what music we should listen to. He waited on me with cocktails and cooking. But not even a friendly kiss when I walked through the door. I clocked it. We ate baked Morning Star Chicken Patties over a salad with croutons and homemade caesar dressing. He told me “my wife used to make this for us and I’m not really a cook, but it tastes good.” I accepted that he cribbed his wife’s recipe for his meal, in light of not being a cook. His cocktails were exceptional and my ice cream sandwiches did not disappoint. It got late as we bantered about music and he hand rolled cigarettes. I was drunk and also nauseous from smoking. He went on and on about his friends in Michigan, their guy times and the fun. “Fun guy,” I thought. But this time I was not thinking,  “I’m fun, I like fun! And I’m casual, I can do casual.” I was tired and wanted to go to sleep. I wondered if this was what he was really like. He gave me his college t-shirt and a pair of pajama bottoms to sleep over. I was anxious wondering if the pants would fit as he was smaller on the bottom than me and the shirt would undoubtedly stretch
M  I  C  H  I   G   A   N  across my double D chest, which was also much wider and larger than his. 

I slept in his room, in his perfectly made bed, with all white sheets and a white down comforter. White walls with more artwork resting on the floors and leaning against the walls and baseboard. We didn’t kiss. I tried to sleep but was too anxious thinking about what I would do in the morning if I had to poop. I worried my hair would be greasy. I didn’t have a toothbrush. And, what if it snowed, I wasn’t prepared. 
I woke up sick in the morning and he made me toast and coffee. He gave me big socks and I held in my poop. My hair wasn’t greasy and I used his toothbrush. Everything was fine and normal. But it wasn’t. I wondered what I was doing there, hungover and wearing his socks and pajamas like the ugly college female best friend. But I accepted it, I went with it. He gave me a scarf to wear home. He walked me to the train. A peck on the lips. My friends warned me “This is not good. Something isn’t right. But if you think you can handle how this is going to end, then go for it.”