The Time I Went on a Date with a Homeless Woman
I remember her OKCupid profile, even though we only went on one date, and it was nearly 15 years ago. MixTapeGirl. What a cool name. Tapes hadn't been used in like 20 years, so this meant she was probably my age, into music, and had a sense of humor.
This was before online dating was popular. There were no apps. It was done on websites, and there were four: Match, E-Harmony, OKCupid, and Plenty of Fish.
I was in my late twenties, but most of the people on these sites were older divorcees, so I was psyched when I found this cool, attractive, same-aged girl, whose profile was all about bands she liked, that I also loved, and it even said she was a Michigan grad, so she was likely smart and educated. Had I won the lottery?
I'd just moved to a bad part of Oakland, intentionally, since low-income neighborhoods saved me money, but even for me, this area was sketchy. Busted car windows, street fights, and police tape were normal.
I need to back track, or this story won't make sense. I'll save time with an info dump:
1. When I was a kid, I was fat. Like, 5'10" and 270 pounds at 18, which means I had low self-esteem and was afraid to date. I lost all that weight by 19, but that didn't boost my self-esteem.
2. I grew up in the Bay area, which featured an historic homeless population, so it's not a surprise that I grew up wanting to help them. Age and cynicism teach some of us how to step over them and avoid eye contact, but as a kid, that was impossible.
3. I returned to the Bay when I was 27 to get an MFA from an all-women's school that allowed male grad students ($$$), but I was supposed to be at Oregon, getting a master's to work with the homeless. However, after a car hit me and I was in a wheel chair (temporarily), I'd decided to become a writer (homeless joke goes here).
This explains why I a) had a soft spot for the homeless, b) was living in one of the poorest cities in America, c) had low self-esteem, d) was reluctant to date at school (it was allowed, but seemed like a bad idea), and e) crazy enough for this story to be true.
Back to that day in 2009. It started out normal. I logged into OKCupid to see how many girls had not replied to me, and instead, I saw an email from "MixTapeGirl" with a simple message: "You seem smart and cool. Wanna take me out?"
RECORD SCREECH.
Take you out? How about we get married? And now. Like, based alone on the fact that you are sentient, have good taste, and a hot pic. Seriously. Justice of Peace. Now. I'm not kidding. OK?
I calmed myself down with a quick walk and a cigarette, wishing for the hundredth time I could quit so I wouldn't have to lie about my habit on first dates, then ran back inside to log into the site and compose a masterful message to seal the deal.
It worked! She replied a day later (normal before smart phones) writing, "Why don't you pick me up this Saturday and we can take a walk and get to know each other? You can find me at XXX Harrison Street. Buzz when you get here and ask for me.”
I blinked and shook my head. The address had to be a mistake. It wasn't just that it was in a commercial area of Oakland, but it was a really bad part. Like, one you don't drive to, through, or park in, unless you're a cop or an idiot.
My brain said, Something’s off, so I replied, "Why don't we meet at a coffee shop?"
"Sorry. My friend wants to screen you."