Boston Boyfriend / Jay Francis Warren

Leaving California was the best and worst decision of my life. I learned the importance of seasons, the difference between being kind and nice, and that wicked is an adverb most closely related to “very” in Boston unless you’re talking about the musical. Leaving the Bay Area (aka The Bay) was the first time I had ever not lived in California, add in medical residency at BU and it’s a whole new adventure.

The first few weeks were rather daunting; everyone walked and spoke so fast it was hard to not feel behind every second of each day. I cried by myself more than I’d like to admit. The people were wicked kind though, (see what I did there!); always willing to help even though they would kind of half-jokingly ask where I’m from and when I said California they would say “fuck the Dodgers/Lakers”. Then I would say “I’m from the Bay actually” and they would act like they have never heard of that until I said San Francisco. They did not care for San Francisco much aside from saying “I loved Full House” which is funny considering that show ended before I was even born.

In the first few weeks I went out to bars and clubs with my cohort. I met the same men over and over again; they would all offer to buy me a drink and then talk about themselves. How much they love private equity, their dad’s boat, and how they want a “traditional” wife. When I told them I was a resident you could feel their hesitance, as if their intelligence was being challenged - it made me laugh every time.

After three straight weekends that felt like one big time loop, I downloaded a couple dating apps to see what else this city could offer. It began feeling similar to the bars but with more evidence of how much they loved golf or fishing. This was until I saw a profile that reminded me of home, he did not look like your typical Boston boy.

This profile claimed to be over six feet tall, tan complexion, solid jawline, and rather funny prompts. His name was unique enough that I was able to find his Instagram easily and there were some pink but no red flags, it seemed like he just had fun on social media if anything. The greenest of them all was he posted stories of songs that I knew and liked after checking them out. This is rather cheesy but the fact he posted Jorja Smith covering Frank Ocean’s “Lost” made me feel as though I had been found.

Since I was in my bold era, I figured I would send the like and to be even bolder, message him first. Back home I was always the friend giving dating advice, but this time I needed it. When friends would eventually ask about my dating life, I would say “coaches don’t play”. But this time it was my turn at the play ball… and I needed a coach. So, I called my best friend back home.

As she told me this guy was worth it, we began coming up with and laughing at our own cheesy pick-up lines until she said the funniest line “he looks like he listens to more Drake than Kanye (this was 2021 mind you, that Drake/Kendrick rap beef wasn’t even a thought yet). Without hesitation I sent it and three dots immediately popped on the screen.

He did not make it more than 3 hours without asking when he could take me out. Those words mattered a lot to me because even as a strong, independent woman being asked “let’s meet up for drinks” lacks the romanticism I was looking for in a man. We decided on the following Friday and then he smoothly got my number so we could move our conversation off of the app.

On the Thursday before our date I told him how stressed I was with life and he Facetime’d me without hesitation. He led off with “I figured you would want someone to vent about Boston who knows Boston and isn’t someone you spend all your time in residency so they don’t think you’re weird”. I hadn’t even met him yet and he seemed to understand me already. Our date came Friday and at 7 on the dot he called me, I panicked and answered frantically screaming from across my bedroom “I AM ALMOST READY” and he calmly said “okay at least I am not the one to start panicking first, I missed a turn and I am running ten minutes late, also my friend is in the backseat cause they needed a ride to where we are going” to which I laughed and said perfect.

His friend was a woman he made music with as he was dropping her off to her boyfriend’s place who he was friends with, another green flag. We went to this Mexican restaurant in Southie and while we waited for our table I couldn’t help but realize he was SO MUCH taller than I expected (he was taller than my brother who is like 6’2) and I started getting nervous asking rapid fire questions. He carried himself very calmly and laughed saying “didn’t realize you were Larry King interviewing me with all these questions”. He wouldn’t admit it then but later I found out he was also very nervous and blurted out his first thought without thinking.

We both began laughing hysterically as we entered a place with more white people than I had ever seen. Not that important of a detail but we were probably the only non-white people in there at the time. Hours go by and as the night closes a woman being followed by what I assumed was her boyfriend came up to our window as his hands went into his palms she yells “YOU’RE TOO BEAUTIFUL FOR HIM” a drunk woman exclaims pounding on the glass. Her boyfriend apologizes and tries to walk her down the street. My date looks over and goes “those are two of my best friends I have known forever, I told them we had a date here tonight, so I am guessing they wanted to see if we were still here on the way back to their apartment”.

Based on how his tan complexion turned beet red I know he did not plan it, but it felt kismet anyway. After bringing him back to my apartment where he left me more than pleasantly surprised I knew I needed to see him again. A week later he shaved his beard that he had on our first date which made him dangerously more handsome and made me even more swoon. I decided right then I wanted this to be my man of Boston. He would come up with new great dates all the time from comedy shows, to Red Sox Yankee tickets behind home plate, concerts, random Sunday drives to new places in New England and most importantly dinners at hole in the walls that would become favorites as only locals knew them. For the first time in a long time, I was genuinely in love. When he would leave and I was all alone again I would cry because his presence made Boston feel like my home and when he left that feeling went too. .

Soon enough I was meeting his friends who all embraced me into the group and would joke about how quirky he was, but they loved that about him & I did too. He had some quirks like a love for spliffs, occasionally drinking too much, making R&B music, and Hawaiian pizza with jalapenos. The last one slowly became something I loved too, and it made me love him even more for it.

After a few months it was rather important for him that I attended this family event. I don’t think he made it three weeks without asking when I could be his girlfriend to which I was elated but the coach in the back of my brain told me to wait. I said “a few months, meeting your family or both” … this just so happened to be both so queue a man looking like a boy getting his first taste of ice cream. As he drove us back, I could feel his excitement as he described each family member who would be there. He has a big family like mine, so I did not bother keeping track. After he was driving us back from a lovely dinner he asked the same question he did three weeks in and I said, “yes and also I love you” to which he responded, “I keep falling in love with you and I hope it never ends”.

Time carried on and eventually we would go through it all together, he flew out to meet my family in California, and it was a great visit! For our one-year anniversary we went to New York, and it was lovely, but we had some fights which a lot of couples do, it wasn’t until our second trip to California that it hit me. He did not love California the way I did, and by that, I mean he truly was a New England boy. He asked “why does everything look like a strip mall” in LA and it clicked he did not want to live out here like I did once I finished residency. When we got back to Boston, I broached my concern to which he said he would follow me anywhere, but it felt hollow.

As time carried on, I began feeling like I did in my first weeks in Boston… alone. His company did not provide the warmth it once did as it felt fleeting. I thought back to when I first met his uncle who said “don’t change him or yourself, love each other for who you are” which was ringing like a gong in my head. It was so loud I became reserved amongst my peers, quieter than usual.

I kept trying to draw our future together in my mind, but it only became more apparent how different we are as people. Culturally we were raised so vastly different growing up around people my parents immigrated with whereas he grew up in a mixed household with multiple cultural influences. Not that one is better than the other, but he did not plan on the Bay area life for his family, and I did not intend on New England for mine. I would cry every night over him knowing I needed to end things so he could find his person.

My feelings were obviously hurting too but it felt as though I was hurting him twice as much as myself which made me cry more. After two years of love that had gone every which way from up, down, sideways, back and forth it now needed to end and I would lose my best friend in Boston. It hurt so much but I knew we would both be better for it. When I sat him down on my tiny Amazon couch (that he assembled with me) and said this you would have thought I shot his dog in front of him. I take that back only because he loves that tiny wiener dog more than literally anyone or thing, but you get my point. I began crying again, we had sex again, and then again crying, then he left.

I know in the end I hurt him more than he could have hurt me, and in turn that hurt me to think I could do that to someone I love, but I was right. I wrote this to eulogize my love for my Boston Boyfriend, because while he was perfect, we weren’t and I hope he finds the person that can recognize that in him like I have found now back in California.