I'm in love with my MD

Some context: I’m a senior at a big state school (UMich/UT/UVA/IU Kelley, not saying which) and an incoming analyst at an EB (EVR/Moelis/PWP/Roths). I’m a guy, he’s a guy. I’m not out at work, so please don’t try to figure out who this is.

Winter break of junior year I was staying in NY for a few weeks and got lonely, so I downloaded Hinge. I matched with someone older than my usual type, mid/late 30s. My roommate said this is a daddy issues thing. I talk to my dad every Sunday. 

We got drinks at a really nice bar in Flatiron. He was genuinely one of the nicest people I’ve ever met. Easy to talk to, handsome, asked a lot of questions about me. It wasn’t until the third drink that I found out he was an MD. We closed out the bar. He walked me to the subway and didn’t try anything, which somehow made it worse.

I had completely struck out in SA recruiting that year and I made a conscious choice not to bring it up. I didn’t want that to be what this was. He brought it up himself. He asked what I was thinking professionally, and when I told him, he said he could “put me in front of some people.” I thought he was being polite.

Next morning I had an email from HR about an off-cycle spot that had opened up for the summer. I went back and forth for a day about whether taking it was weird. I took it.

To be clear, I interviewed like everyone else. Four rounds plus a superday, and I prepped harder than I did the entire fall. I don’t think he pulled for me. I’ve never asked.

The summer itself: worked harder than I’ve ever worked. Got staffed on one of his deals, and if anything he was tougher on me than on the other interns. He tore apart my first CIM draft in front of the VP. Honestly it made me respect him more. I’d take the long way to the kitchen just to walk past his office just to see him. I know how that sounds. Some nights we’d be the last two on the floor, and he’d call me over to his office at 1am to flip through a page and he’d hold eye contact there a little longer than he needed to. Neither of us ever said anything.

Last week of the summer the team went out for drinks. People left one by one and eventually it was just the two of us. I had way too much to drink. He kept ordering old fashioneds and I kept matching him, which in hindsight was a terrible decision for a 21-year-old who had eaten half a Sweetgreen bowl that day. It got flirty. 

And then I leaned in and kissed him. 

I leaned across a bar table and kissed a Managing Director at my bank. Nobody on this forum has ever made a worse risk-adjusted decision. I watched my entire career flash before my eyes in that split second. Then he kissed back. Then he pulled away, said “we shouldn’t,” and called me an Uber. I know. I did not sleep that night. 

At 7:40am he sent me comments on a teaser like nothing happened. We have not talked about it since. Sometimes in meetings I catch him looking at me and he’s always the first to look away.

Before I left I got him a nice whiskey bottle and a handwritten card. He took me out for a drink after and mentioned, out of nowhere, that he’d been single for a while. I genuinely can’t tell if that meant something or if he was just talking. When we said bye he hugged me a second longer than normal. I replayed it the whole flight home.

Got the return offer. He was the first person to text me congrats, before my own analyst did. It just said “Proud of you.” I’ve reread it more times than my offer letter.

I start full time next summer and I have no idea what to do. I’ve been thinking about this (and him) everyday since the internship ended. Is this something that can actually work? Has anyone here dated someone senior at their bank? Do I need to tell HR if we do decide to start dating? I’m not trying to blow up my career over this, but I also can’t stop thinking about him.