I accidentally dated a homeless person: Part 2 •

Michaela Lassig
6 min readSep 1, 2015

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So I drove 7 hours after work on a Friday to go to Mammoth. The night happened; the morning came. When I woke up in Mammoth, I freaked out a little bit. A lot bit. My heart was racing and my mind was dizzy with ‘what ifs’ and spinning red with a parade of red flags which I ignored.

Let me tell you what happened that night in Mammoth.

I finally get to the bar that Chris told me to meet him, and he is drunk and he is excited to see me. I’m suddenly shy, nervous, and overwhelmed. Over the course of the night we drink, we kiss, he cuddles me, I cross my arms, we have a generally good time but I’m a little bit on high alert so I try to drown that out with vodka sodas.

I didn’t realize this at the time, but Chris was wasted. Like blackout wasted. I was close behind him. We get back to the hotel and I’m not ready to have sex or be at all intimate yet. I still feel like I don’t know him and that there’s something he’s not telling me. So I sit on our couch in the room, pat the area next to me and say ‘come sit’ and he does. So obedient. He stares at me with these heart-filled, glazed-over eyes and says ‘god you’re so beautiful’ and he tries to go in for a kiss. I push him away and say quietly,

“Chris, let’s talk. I need to know more. I’m not ready to get in bed with you. Tell me why you’re on the trail! What made you do the PCT?”

His body noticeably reacts to this question and he lets go of my gaze. Tears fill his eyes and he slowly tells me that his girlfriend died of an overdose and it was his fault. I think he also said that he was in jail for it for like a few months too but I’m not totally sure because I’m a bit inebriated and I’m in shock and I’m trying to process this information. In my mind questions are swirling like a goddamn tornado…what kind of drugs? How could you have killed something? Was it heroine? Did you share needles? Did you just buy her the drugs? How are you implicated?

Oh my god. Do you have AIDS? How will you ever get a job? Are you an addict? WHAT THE FUCK DID I GET MYSELF INTO?

Instead of verbalizing any of this, I look at him and say, “i’m sure it wasn’t your fault” and he is bawling saying that it was. I ask him to tell me more but he doesn’t want to. He also tells me I remind him of her. perfect. I remind him of the dead girlfriend he might have accidentally had a hand in killing. (Red flag) I comfort him and kiss him and you’ll never believe the fucking stupid shit I did next. I fucked him.

I’ve always lived on the edge this way. It’s shocking that I don’t have any terrible diseases. I’m sure some psychiatrist would have something to say about this but anyways…I asked Chris when his last STD test was (and I asked him about AIDS) and he said it was clean and taken in January and that he is sure he’s clean. Then he asks me the same and I think, actually I haven’t had one in like 2 years. I tell him this and say that it’s up to him because I think I’m clean but I don’t know. (Who knew I’d be the delinquent one on this line of questioning). We hook up. It’s great. I let myself be in the dark moment and not think about anything except what we’re doing. The next morning, my throat catches in that dry way it does when you’re dehydrated from a night of excess alcohol consumption, and I wake up with a start. What time is it?! I have to be back in San Jose by 4pm for a dress fitting with my best friend for her wedding. But it’s still early. It’s 7am. I take my dog out for a walk and call my friend Eleni. She’s on my level for blindly dating and always has good advice and low judgement levels. We talk through everything (except the unprotected part and the dead girlfriend part because I’m too ashamed). She thinks I should drop him but she’s being supportive. I can tell.

Ok so, we drive towards San Francisco. I look over at him and (I know this is fucking rude) but my thoughts are that I’d be embarrassed to be seen with him on the streets of SF wearing those clothes and then I wonder out loud ‘how many pairs of underwear do you have?’ As it turns out, 1.

He has 1 pair of underwear.

The closer we get to the city, the more I feel like dropping him off on the side of the road and bolting. But we get to the apartment. I drop him off in my tiny closet of a room and hand him a towel and say “here’s a towel in case you feel like showering immediately” and I gather all of my personal items that are important to me, leave this stranger in my apartment, and speed off to my appointment. (red flag)

On my way back from my appointment I went to Target and picked Chris up some jeans, a t shirt, a cute plaid button down, and some underwear. I knew this was presumptuous and I was nervous that when I showed up with some clothing that he didn’t pick out, that I’d get a good yelling at. But, when I presented my goods, instead of being pissed, he was super grateful…as homeless people generally are when you buy them things. (Red flag)

A learning moment for me, when you’re on the trail for so long and when you grow up on your own with little supervision, there are certain hygiene and emily post etiquette shit that you don’t pick up.

I had to tell him to brush his teeth on MULTIPLE OCCASIONS I really did. He wouldn’t have done it otherwise. One time I asked him if he’d brushed, and he reluctantly said no, and then went to go do it. He came back 30 sec later and said “all done!” and I said you’re lying! You just swished with mouthwash. He hung his head and said, ‘so! It’s the same thing.’

Is gingivitis contagious? Is it basically a mouth STD?! Can I get it?!

Also, I made him floss. HE HAD NEVER FLOSSED IN HIS LIFE AND HE’S 37. How gross is that? I also wondered if his stained teeth were in a meth stage or if it was just neglect. How can you tell?

So all week we had sex, brushed our teeth (with my supervision), went to bed, had sex and then he would walk my dog and wander around the city for the day while I was at work. I think sometimes he would sit on a bench, starving, waiting for me to come home for hours.

In the middle of the week, we were drinking a bottle of wine, and he asked me “are you afraid of me?” and I was totally taken aback by this poignant question. “Umm yeah well, maybe?” We had a talk about feelings etc and he said that he thought I was his soulmate so it was going to work out even if we needed to move slowly and also that he didn’t have to be here. He would be fine. That calmed me down a little bit, except for the soulmate part, and I did a bit of thinking.

The next night, right after he told me he had an earache and was going to try to drain it (in my room), I told him it was time to go. I was heading to Soda Springs for the weekend and he could get a ride. He was fine with it. He even wrote me a spreadsheet showing which towns he would have cell service in. It was a very generous gesture which I completely disregarded/downplayed because I was done.

Current status: he calls and texts me and I barely respond. In fact the first night, he texted me that he loved me. I told him he didn’t know me. I looked up his criminal record online finally. A little bit scary. But at least, he hadn’t lied.

Part 3: After I dropped him off, and how I Caspered (friendly ghost)

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Michaela Lassig

“The more embarrassing the story, the less embarrassed I become.” — Me