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."

"What?"

"Online dating is scary for girls. I promise I'm real and normal. I'm just careful. Please trust me. My name is Sara and I really want to meet you."

"Can I have your number? Just in case I’m running late?"

"I don’t have a phone right now. When we meet, I'll explain everything. OK?"

If you don't understand why I was desperate and said yes, I guess you've never met anyone that was fat in high school, has a bleeding heart for the down-and-out, and has been looking for his soul mate since before he knew the words "soul" and "mate."

“OK. See you Saturday,” I wrote, wondering how I was going to lie my way out of this. But I couldn’t. I had too much desperation. I MEAN HOPE! TOO MUCH HOPE!

Not one to quit (or listen to intuition, apparently), I left early to find parking, and I quickly saw that 1. the neighborhood was worse than I'd pictured, but nothing I hadn't seen before, and 2. She’d 1000% given me the address of a homeless shelter.

I parked my car at a busted meter in front of a KFC-Taco-Hut bordered by two rival Cash ’Til Pay Day marts, across the street from three bodegas, each catering to a different race.

I popped a breath mint in my mouth and hoped it'd cover the last-minute cigarette I'd huffed before driving there, got out, and walked to the shelter, which looked like a prison. I stared at the handleless door until I noticed a cloud of smoke to my right with six men who collectively weighed 2,000 pounds, pointing and laughing at me.

"Can we help you?" one of them asked.

"Um. Yeah. Um, I'm here to meet Sara?" I asked-said, resenting my timidity.

"SARA?" the largest, most on-the-verge of death guy asked me, waddle-wiggling off his concrete bench to traipse the fake lawn towards me. "Are you sure?"

I looked around, not nervous, but insulted, hoping someone would see me and say, "Of course he's here for Sara. Can't you see he's a sapiosexually cool guy with good taste, like her, and they're destined lovers?" Alas, I only got stares and smoker coughs.

I looked at the intimidating steel door ahead of me and back at the slightly less intimidating man who was now so close to me that I could smell alcohol whistling from his pores. "Um, Yeah. Is she...Is Sara here?"

"Who you?" [not a typo]

"I'm...I'm Mike."

"OOOOOOOOOH! It's MIKE" a man from the smoker's lounge said unironically. "Tell Sara Mike's here. She'll be COUGH PHLEGM SPIT COUGH SLAM FIST INTO HEART COUGH HUGE LOUD SNOT INHALE LOOGIE SPIT COUGH..."

The man in front of me crossed and uncrossed his eyes, then hit a button on a steel panel a few feet from the door that I hadn't seen, and we heard a buzz. He threw his lit cigarette on the fake lawn and pushed the door, walked in, and I followed him into a cold, tiny, windowless chamber. There was no signage outside or in here, but based on the crew outside, I was wondering if this was an asylum, not a shelter. Should I leave?

The man faced me and stuck out his hand for a shake. "I'm Ron. Sara's Dad."

I'm no DNA expert, but it seemed unlikely this guy was her Dad. I nevertheless shook his calloused, sweaty hand and pretended I was on board for whatever came next.

"Before you take our daughter out"—Yes, he said our—"What are your plans?"

I smiled, expecting to melt his angry facade, but I'd misread Sara's father. Instead of a boisterous "we're friends now" laugh, his eyes narrowed and his grip tightened.

"I'm, uh, here to go on a walk.” I let my hand go limp to signal the end of the shake, but he didn’t release. “And I hope we hit it off?" I added with no confidence whatsoever.

I blinked, hoping there was more. But a beat passed and nothing changed. I tried to pull my hand away, but he didn’t let me, and the room’s stale air and his body odor were now waging a war against his skin-pore-alcohol-cologne.

"Um, are we cool?" I finally asked.

He scowled then released my hand and thwacked me HARD on my back. “Yeah. We cool." He smiled, but we both knew it wasn't sincere. You got a buck?” He eyed my pocket to make sure we both knew he recognized the wallet shape in it.

"Uh, sure," I replied. But before I could pull out my wallet, the door buzzed and opened.

This is the point in my fairytale mind where my princess emerges, a perfect amalgamation of all I've wanted and imagined (and then some). Alas, this is Mike Oppenheim's Desperate Date with a Homeless Woman, so this is what happened:

A girl my age emerged, but she did not match her picture. I mean, it was her, but something had gone very, very wrong. She was 100 pounds overweight and dressed in frumpy sweat pants and a loose Minnie Mouse sweatshirt, and as I looked down to hide my disappointment, I noticed she was wearing thick wool socks in Crocs.

Ron stuck his thumb at me and laughed. "You sure you wanna go out with THIS guy, Sara?" 

She smiled at him, then me. “C'mon, Ron, he’s sweet. Can’t you tell?”

That's when I knew I was properly screwed. Because if there's one thing I can't say no to, it's genuine kindness, and Sara and her warm smile reeked of it.

"Nice to meet you," she said, putting out her hand.

We shook and I tried to smile, but all I could think about was how close I was to puking thanks to Ron's B.O. and booze potpourri.

"How about that buck?" Ron asked me.

"Ron!" Sara pushed him toward the exit and he shook his head as he left. "I hope you don't mind that I smoke," she said, holding the door for me to follow him.

"Not at all! Actually, I do too,” I said, holding the door and nodding at it. “Ladies first.”

"Sara!" The gang of smokers yelled from the fake lawn patio hell zone as we emerged.

She waved and led me to their den, where the smoke was too dank, even for me, a smoker of ten years.

"Can I borrow some money?" one of them asked me.

"Do you have a smoke?" another asked, holding a freshly lit cigarette.

"Guys! I just wanted to introduce you. This is Mike. He's my date, and we're going to go out for a while. Don’t wait up," she said with a wink.

No one laughed or smiled, but one of them did look at me with intentional intimidation, saying, "Sara is special, Mike. Behave."

This sent the group into hysterics and Sara gave a curtsy. "He's cool, guys. Be nice."

Ron asked for a dollar again and I lied, saying I’d give him one after I got to an ATM, and Sara grabbed my hand and wriggled us away to the street where she pointed at a fourth bodega I hadn't noticed, three doors down from the KFC-Taco-Hut across the street. "Can we hit that up before we take a walk? I'm out of cigarettes."

"Sure," I said, wishing I hadn’t left my pack in my car. My pragmatism radar was on full alert and even though my ride wasn’t nice, I didn't want the men across the street to know I owned a car. 

We entered the bodega and she made a bee line to the candy rack, grabbed four chocolate bars and a pack of pop tarts, then walked confidently to the soda cooler, took out two 32-ounce Diet Pepsi's, and looked at me. "You want anything?"

"Uh, no. I'm OK," I said.

She shrugged. "We can share." She marched to the counter and asked the clerk for two packs of Marlboro 100s (extra-long cigs), and pointed at me. "And whatever he wants."

"Camel Lights, please," I said, feeling awkward about my date buying me cigarettes.

The clerk studied us for a second before pulling the packs from the storage spot above and putting them on the counter. He said, "Twenty-four dollars," a number that didn't reflect any calculation and seemed to be "too even" for a bunch of items with sales tax.

Sara stepped to the side and showed me coy eyes that had probably worked long ago, but now she was a poorly kempt hobo in a Disney sweatshirt.

I took out my wallet and leaned in so she couldn't see my billfold, but all I had were twenties, so she knew I had at least sixteen dollars when I got my change.

She led the way out, but stopped in front of the exit at a rectangular cooler on the floor, stacked with pints of ice cream and other frozen desserts. "Oooooh my favorite!" she exclaimed. After rummaging for what felt like an eternity, she said, "I need help, Mike."

"Huh?" I asked, busy failing to plan a polite escape from this awkward fiasco.

She began handing me pints of ice cream and other packages of frozen delights, too many for me to hold, so I started to set some down but the clerk yelled, "That's enough, lady! I warned you last time! No more! You get out! Now! Don’t come back!"

She dropped a pint on the floor so she could give him the finger, and said, “Let’s go!” 

I started cleaning up, but she grabbed my hand and pulled me to the door, giggling, and when we got outside she said, "Be right back."

I thought about running away as I watched her cross the street to return to the smoker's patio, but I didn’t want to offend her or make any enemies, so I stayed put as she handed Ron one of the Pepsi’s, two candy bars, and her second pack of smokes. 

She came back, all smiles, and pointed at the KFC-Taco-Hut. "Shall we dine?"

"Uh, let's take a walk first. Have a smoke," I said, figuring I could end things soon.

She put a fresh 100 in her mouth and made a cute expression with pursed lips. 
"You got a light, handsome?"

I lit her cigarette, then one of my own, and she took my hand again and led me toward a small, unkempt park littered with trash and tents. Her hand was sweaty and I felt no electricity, but as she tried to sell me on this neighborhood and its creature comforts, I could tell she was once a total catch and still had a clever mind.

"So, uh, you're probably wondering why I'm HERE.” she gestured at the shelter behind us as she sat on a swing.

"Um. Yeah," I said, eyeing two non-homeless kids on a bench glaring at us.

She patted the empty swing next to her. "Sit and I'll explain everything.”

With eloquence, college diction, and sharp wit, she proceeded to tell me one of the longest, saddest stories I've ever heard, explaining how an assault on campus ten years before had led to a mental breakdown that led to an arrest which led to moving back in with her verbally abusive, alcoholic mom until she couldn’t take it and left, even though it meant sleeping on the streets until her application for state funding was approved and she could move into this shelter. She said she was grateful, because even though she’d gained all that weight, she was clean now and it was better than using. Besides, if we started dating, she could turn things around, lose that weight, and make me very happy.

It was like a job interview, but, thanks mainly to Ron, I wasn’t gonna bite, even though her story was undeniably sad and made me wish I could help. It was just too much drama, even for a formerly fat, hopeless, bleeding heart romantic.

We sat in silence until she rubbed my leg. It was supposed to be sexy, but it wasn't.

I got up, stubbed my cigarette with my shoe and put out my hand, nodding at her nearly-finished cigarette. "I'll throw our butts away."

She shook her head and pulled out a new cigarette and lit it with the end of her current one, then tossed the old one on the ground and we watched it burn on the clumpy, mostly dirt grass-patch in front of the swings.

Eventually, she patted the empty swing. "Sit and have another one, cutie.” 

I obeyed and couldn’t believe that I’d gotten into an MFA fiction program but couldn’t invent a good enough lie to get the hell out of there.

She took a long pull from her Diet Pepsi and offered me a sip.

I declined and could tell it offended her.

She stood. "Look. I know this is weird," she said kindly, but with great emotion. "But we could just, like, keep this casual. Like, if you let me spend nights with you, I’ll take care of you, and we can, you know." She accented this with an expression that ruled out any confusion over exactly what her euphemistic language was meant to convey.

I looked at her still-burning butt on the grass, trying its best to piss off Smokey the Bear, and said, I'm sorry. I mean, you seem nice, and I was hoping we'd hit things off, but—"

"It's because I'm fat!" She started crying.

No, it's because you're mentally unsound, I'm a grad student in debt, and while I want to help the homeless, your posse, which keeps pointing at us and making me feel uncomfortable, terrifies me and I have a strong feeling you’re sincere, but to them, this is a set up.

"No, Sara. This has nothing to do with looks, or personality, and while I'm really sorry for what happened to you, especially with your mom and your loans, I just can't..."

She was really bummed after this, so I agreed to her request that I buy her KFC and another four packs of cigarettes, but when she then asked me to take a drive so we could go to her favorite thrift store, I pretended I was tired and told her I had to go.

She asked to see my car, so I lied and said I’d taken BART (the subway), even though she knew from my email that I was driving there since I’d said I would take us to dinner that night if we hit things off. This meant I had to walk to the BART station after I returned her to Ron (who took a few more dollars from me), where I then waited fifteen minutes before sneaking back from the other direction to get my car.

She never contacted me again, and I've rarely thought about her since, but every once in a while, I hear or see something about homeless people and the memory surfaces, and I wonder if MixTapeGirl ever thinks about her date with MFAMike and if she ever got her life together.

We now live we in a society engaged with mental illness, but it wasn't like that back then, and I can't help but wonder if she would have had a better fate if she'd grown up in today's world, where children are encouraged to speak about their psychology and mental health services are not only more affordable, but available on apps.

I don't know, and I probably never will, but I do know that this experience changed me, so I hope my re-telling of it does something for you. There's no panacea for mental illness or poverty, but a little compassion and mindfulness can go a long way.

Every homeless person was once a child, wide-eyed and needy, depending on someone to feed, cloth, and nurture them. But something went wrong after that, and while it's not your job to do anything about that, it is my job to make you think about your relationship to these issues.