Anthony and I met in January of 2023 in a cocktail bar in NYC. His hinge profile was quite confusing ("NYC / Miami / Puerto Rico). Needless to say, I wasn't sure where the man actually lived.

Turns out Anthony was living in Puerto Rico, and flying to Miami and Puerto Rico to date. I wasn't planning on getting myself into a long distance relationship but unfortunately for me, the date went fantastically well. And the second date? Even better. And after the third date in one week (with multiple push backs of his flight and extensions of his hotel room) Anthony asked me like a weirdo "I am no longer planning to see anyone else, how would you like me to pursue you?" And after two and a half years of lackluster casual dating in NYC, I shockingly found it quite endearing.

I was finally excited to see texts from someone pop up on my phone again. After leaving each other after our three-dates-in-one-week-palooza, I reached my soaking wet hand out of the shower to read what it said.

But then .... a week went by. And like every cautious dater, I let the doubt creep in. What kind, smart, handsome, (very) tall man could still be single and have nothing wrong with him? He was sending me photos from Puerto Rico (specifically the one below) saying "working from home."

I worked myself up all week that it was too good to be true and that the shoe would drop eventually. And then Friday as I was getting ready for him to come over to cook dinner, I realized what was wrong with him... he was homeless. He didn't actually live in Puerto Rico. He lived on the streets of NYC and he was sending me stock images throughout the week to throw me off. I alerted my sister/roomie immediately and insisted she stayed in the apartment for the first few hours to make sure everything was okay.

When Anthony arrived, rolling luggage and all, one of the first things out of his mouth was "Do you mind if I shower and throw some laundry in?" SHOE. DROP. He was officially homeless. My radar was correct.

When my homeless date hopped in the shower, I hopped into my sister's room and we laid on our backs just laughing at the insanity of it all.

Anthony and I started cooking dinner and after an hour of laughing and remembering how great we vibed, I decided to dismiss my sister and I asked Anthony if we could talk. I hesitantly asked him why he needed to do laundry and shower. I gave him a safe place to tell me about his homeless life. He told me his water got turned off in Puerto Rico that week because his landlord forgot to pay the bill and that he always liked to shower after flights. Likely story, I thought. He was ready for those questions.

Anthony could sense my unease and asked what was wrong. And that's when I straight up asked him. To which he proceeded to laugh out loud and pull out his laptop. Immediately upon him opening his laptop, I noticed the Delta WiFi screen pop up, and I let out an audible sigh of relief. He spent the next hour showing me proof of his existence of life NOT on the streets. Because: Homeless Until Proven Otherwise, am I right??

At that point I felt a bit worried that I made Anthony feel bad. That I could even question that of him. Turns out, he found it very endearing. You're never sure if someone is dating you for the right reasons. But the fact that I might have been able to look past the minor detail of him being homeless meant I really truly liked Anthony for Anthony.

PS: After visiting Anthony in Puerto Rico... turns out I am the one closer to homeless with my shoebox Manhattan apartment 😂