His profile reads “I don’t want to go out with you, because frankly I don’t want to go out with anyone. I work six days a week and on my one day off, I drink alone with my cat. I work too much, I drink too much, and don’t worry, I smoke too much as well. I’m cranky most of the time, and I’m sure you’re not surprised. At least I’m being honest. I hope to hear from you, but I’m sure I won’t.”
This was quite possibly the worst personal ad I’d ever read. So naturally I thought, I have to meet this guy.
I’d been single as long as I’d been living in Chicago, which wasn’t long, but I was already burned out on looking for love on the internet. I was often determined to be too salty for your average guy, plus I wasn’t looking for your average guy anyway. I’d been on a good handful of ho hum dates with guys who seemed to be looking for someone shorter or taller or thinner or meatier or quieter or louder or less opinionated or more traditional. They were decidedly looking for someone who wasn’t me, which was fine as I didn’t feel many sparks along the way either. I convinced myself that finding “the one” was bullshit, and it would be much more fun to just dabble in interesting people. I had good friends, did I really need a soul mate when it was so much easier to be an interpersonal adventurer? I would be a relationship taste tester, a far more attainable title than life partner.
So I send a response to the worst ad ever, thinking, I’m salty, he’s bitter, perhaps we could be two great tastes that taste great together.
He answers quickly, saying not only had very few people responded to his ad, but the administrators of the website took the time to advise him that his ad was truly awful. Color me amused. We message back and forth a few times, and he is unexpectedly charming. He mentions his next day off was the following Tuesday, and was I busy?
That particular Tuesday was the 4th of August, also known as my birthday, but I had no plans. I tell him I’m available like it is any other Tuesday.
He asks me to pick the time and the place, saying it’s important that I meet him in a location where I feel comfortable meeting a stranger, preferably in my neighborhood so it’s convenient for me. If you’ve spent even one minute dating on the internet, you know that this sort of consideration is a rarity and should be appreciated. I choose Simone’s, a bar in Pilsen, a casual spot with a solid beer list, decent empanadas, and a vintage soul soundtrack. I ask him if he’d like to see a picture of me before we meet as I don’t have one attached to my ad. He says “No, it’ll be more fun this way. Plus, it doesn’t really matter.”
He shows up at Simone’s on time and he looks just like his picture, another internet dating miracle. He’s handsome in a rugged, James Woods before he went all fucking crazy kind of way; he’s all man without a hint of prettiness. He's wearing a pale pink woven shirt with a pack of yellow American Spirits in the pocket. He kisses me on the cheek when he introduces himself, and it’s not creepy in the slightest. Perhaps he pulls it off because he’s a supremely confident Argentinian guy named Juan.
Juan and I order lunch and drinks and we discuss how terrible his ad is. “But it’s all true”, he insists. I am absolutely tickled to be on a date with the most undateable man in Chicago. We talk about relationships and how we both almost got married but it somehow all slipped away. We laugh and drink beer and make effortless banter about all of life’s questions, both great and small.
As we finish up, he says “Your profile says you’re a Leo. That means your birthday just happened or maybe it’s soon.”
“Actually, it’s today.”
“You’ve got to be kidding me. Why didn’t you tell me before now?”
“It’s fine, it’s not a big deal.”
“Oh no,” he says, grabbing the check. “It is a big deal. I’m taking you somewhere better than this right now.”
We drive to the West loop and end up at Blackbird, a hip fancy schmancy joint full of high powered Chicagoans who take their dinners quite seriously. We’re both wearing casual first date clothes; jeans and nice shirts that say we care how we look but we're not expecting too much or trying too hard. I feel underdressed at Blackbird, but Juan clearly doesn't notice or give a shit. We sit at the bar and we have fancy schmancy drinks and suddenly it feels like it really is my birthday.
Juan picks up the check again, insisting that I can get drinks next time. I give him a hug and I'm happy there will be a next time when we part company.
Juan finds me a week later and asks me if I can meet him at Castaways, a beach bar that’s all about burgers, ice cream, and tourists with no imagination. It’s a hot day and we sip vodka lemonades and watch some youngsters playing volleyball.
“Thanks for agreeing to meet me here,” Juan says. “I know it’s super cheesy, but it gives me such a perfect summertime vibe.”
I agree and I tell him it’s fine, in fact it’s downright amusing that a self professed grouch like himself would be drawn to someplace so popular and sunny. He laughs and tells me to drink up, because we are going to go watch a White Sox game on television.
“Oh no,” I tell him. “I’m not the right girl for that. I don’t care about sports at all.”
He takes my arm and says, “You’ll like it with me.”
“Ok, Dr. Seuss. Baseball it is.”
We head to Shaw’s Crab House, a traditional steak and seafood joint. We sit at the counter, and everyone knows Juan. I mean, everyone. He makes light hearted chat with the the white jacketed waiters, the bartender, the hosts, and the busboys; he’s clearly adored by all. We order some white wine and a dozen oysters and Juan watches the game with one eye while we make conversation. I ask him how long it’s been since he was in a relationship, he tells me about five years. I ask him what happened, he says he dated a woman for about eight months who he loved dearly. He tells me she spent all of his money while he was with her; on clothes, on food, on booze, on trips to New York, you name it. He tells me it was all fun and games until he was over $10,000 in debt and she left him as he couldn’t afford to keep the party going.
I tell him, “Dude, that sucks. Women like that give the rest of us a bad name. I’m so sorry that happened to you.”
Juan says, “I’m not sorry. I’m not sorry at all.”
“Are you serious? She sounds like a parasitic nightmare.”
“I had the time of my life with her, Eileen. It was my choice to spend all the money, and I loved every second with her. And I couldn’t blame her for leaving, our time together was up. I couldn’t give her what she wanted. Some relationships aren’t built to last, they’re like a goddamn shooting star. You just have to love what you have while you have it.”
“Wow, you’re pretty optimistic for Chicago’s most undateable man.”
He laughs and asks me how I want the filet cooked.
When the steak arrives, he orders a glass of red wine and when I ask for another fork for him, he tells me it won't be necessary. “I don’t eat red meat. I ordered the steak for you. Enjoy it.” And I do.
We sit at Shaw’s for the entirety of the White Sox game, which goes into overtime, so seven hours flies by like it’s no time at all. When we’re finished, I tell him I'll pick up the check as we agreed on our last date. He tells me I can get what’s not covered by his house account, which is less than two dollars. I throw down the tip and note that it's getting dark outside and I can't remember the last time I had such a good time.
He takes me home and kisses me outside my apartment building. I ask him to come upstairs, but he says no.
“I’m not what you need,” he tells me.
“Isn’t that for me to decide?”
He laughs and says, “I suppose you’re right. I guess you’re not what I need. Don’t get me wrong, I really like you and I would love to come upstairs. But I can’t give you anything more than what I’ve given you already.”
We say our goodbyes and I feel confused and dejected as I watch him light a cigarette and disappear into the night.
I saw Juan a few more times. We went to the movies, we had some more drinks. We talked about life and work and current events, but I knew he was right. He was a great date but I found myself wanting more than that, probably because he was an expert at what I was striving to be: unapologetically unavailable. I think I picked him because I thought all of his adverse points would prevent me from getting too attached to him, keeping my relationship taste tester status intact. Maybe in the end being an “interpersonal adventurer” was a delusional euphemism for being a love avoidant asshole who never wants anyone to get too close. It was difficult to be as honest with myself as Juan had been in his ad, especially since the walls I had built were just as unappealing.
So I put an end to the dabbling and I put my heart into going out on lots of dates; some wonderful, some comically horrendous. Juan faded in my memory, until August 4th of the next year, when I received a text from him saying “Feliz cumpleanos, Eileen. I hope you’re doing well.”
Even though I haven’t seen him since 2010, I will never take “Juan” with no last name out of my phone as he texts me kind wishes every year on my birthday, reminding me that some relationships aren’t built to last, and you should love every moment in the presence of a goddamn shooting star.