Random Musings / Sex

I Went On a Date and Had the Opposite of the Best Time Ever

I’m standing next to the hostess station of a very hip restaurant in downtown Chicago. This place is so hip, there’s no sign out front. So hip…that when you walk in the door you’re not actually in the restaurant. You can’t even see the restaurant unless you go through a door that was probably once part of a castle or something. I’m early, which I hate because it gives me time to question my existence and convince myself that I am not suitable for any social function, and least of all dating.

Leaning nonchalantly against the wall, I watch the hostess answer phone calls and turn away every hapless jerk that comes in wondering if there’s anything available before next month. One guy actually tries to flirt with her, and I can see she is having none of it. She looks at these people with such disdain that I didn’t experience when I walked in, so I congratulate myself on at least looking the part of a hip Chicagoan. A woman walks in wearing an outfit similar to my ankle length trousers, satin tank and black blazer, and I feel validated.

As I pick up my phone to see how long this asshole has kept me waiting, it vibrates, indicating that he is walking up now. My heart drops, and I immediately feel myself start to sweat. I’ve always been an anxious person and situations like these are worthy of a full dose of Xanax. Unfortunately, it hasn’t kicked in and my mind races with thoughts of running, or fainting when he gets here because my heart won’t stop racing or why the FUCK do I put myself through these things when I’d much rather be at home in a sweatshirt and masturbation isn’t so bad, right? and oh Jesus he’s not as attractive as I thought okay I can do this wait no I can’t oh shit..

fancy man

His outfit was slightly less Fancy Man than this.

“Rachel? Hi…” Ben is about my height, balding a little with wavy hair slicked back. He’s wearing a white button down and a black velvet blazer. He wears glasses, which has always been a weakness of mine, and for some odd reason his whole ensemble works. We’ve been exchanging emails for over a month, and in my mind this means that it’s okay to hug when we see each other. He freezes up a bit, which pisses me off rather than makes me feel bad. “Have you been waiting long?”

I tell him no, that it’s only been about 10 minutes or so, when it’s actually been about twenty. He walks over to the hostess and gives her his name. He looks and acts like he belongs there which impresses the hostess, and she gives me a slight nod of approval. I’m not sure if she means anything by that, but I assume it’s Girl Code for Guuurrrlll…you got this.

I guess it’s customary for reservations to not mean anything in places like this because she says our table won’t be ready for another 45 minutes. Ben tells her that we’ll be at the bar. He swings open the door I’ve been fascinated with for the past half hour and I immediately realize that I am absolutely out of my element. It’s dark, super dark. And loud. Crowded, too. What’s more, though, is that this place is filled with people who care about being seen; I feel like I’m in an episode of some Housewives show. I feel self-conscious but I walk like I’m one of them as we make our way to the bar. No one seems to notice the outsider.

We sit down and rather than ask me what I want to drink, he orders a cocktail off the menu and says, “Trust me, I think you’ll like it.”

don draper

Pictured: Not the man I was on a date with.

I’m surprised at how much that turns me on. I’m a Strong Independent Woman, but I guess that I’m still susceptible to Don Draper-esque behavior. We flirt on and off, he makes a comment referencing my alcohol tolerance (which is very low) and the probability of this date lasting longer than we think (which has yet to be determined). He talks about his corporate lawyer job, I talk about my library assistant job. Ben acts like he’s interested but I catch him looking at my chest which I feel pretty good about. He orders my second drink from the bartender, and I notice that the bartender isn’t exactly charmed by him. In fact, I’m pretty sure he thinks Ben is an outright dick. I haven’t noticed anything overly dickish about him. Sure, he has a slightly arrogant way about him, but I chalk it up to wanting to portray himself as an Alpha (which, let’s face it, can be ridiculously hot).

Ben leaves to check on our table, and the bartender starts chatting with me. He asks if I’ve ever been here before, and without hesitation I laugh and say no way. Luckily he laughs too and says he understands what I mean. He’s bearded with full-sleeve tattoos. In the past this guy has been more my type than Ben, but I guess as I get older I’m trying to branch out. I tell the bartender that this is our first date and he looks relieved, I think. He sees Ben walking back and bristles in a way only men bristle when they just know. The bartender gives me a sad look and wishes me luck.

Before I can start to analyze that interaction, Ben has his hand on my lower back. I move to get up, thinking he’s guiding me to our table, but he just sits down, leaving his hand on me. This makes me nervous, and I can feel my neck and chest starting to get blotchy. Still, I like the physical contact. Our table will be ready shortly, and he attempts to order me a third drink. I stop him, partly because they’re eighteen bucks a piece, and partly because I am already starting to slur. I flirtatiously remind him that I cannot hold my liquor, and he seems annoyed.

“That’s the point, isn’t it?” he says in a tone that I don’t appreciate. And now I understand what the bartender meant.

I move away from his hand, and I feel my guard going up. Ben senses this too, because he leans away from me. He catches himself, and continues to make friendly conversation. The hostess comes over to us and says that our table is ready whenever we are. He pays for our drinks, making sure I see the array of black-colored credit cards in his leather wallet. I know he has money, he knows I know he has money, and I know he knows that I know what he’s trying to do. I was impressed up until this point. The bartender and I make eye contact and I fight the urge to slip him my number. He winks at me, I smile in return, and allow myself to be guided to the table.

wedge salad

Who the FUCK eats a wedge salad on a date? Not this girl. Except for this one time. And it wasn’t awful.

I’ve already looked at the menu when I was in the cab on the way to the restaurant. I am notoriously indecisive and I wanted to prevent any uncomfortable moments when I tried to order. He asks me what sort of wine I like. I say nothing too dry, nothing too sweet. I catch him rolling his eyes and I’m about 70% done with this whole evening. The waiter comes over and he orders two glasses of something…I have no idea what it is. He also orders two wedge salads without consulting me. I hate wedge salads.

The waiter leaves, and Ben talks more about his family. Every once in a while he asks a question about mine, but it’s only if it’s something he can critique. Our wine and salads come, and I’m pissed because the wine is really fucking amazing, and to my surprise, the salad is too. This stops the conversation for a while and I’m grateful. The waiter comes back and we order our entrees. Thankfully, he doesn’t order for me, because that would have rendered all my preparations useless. I order short rib pasta, and he orders a steak. He makes fun of me for not ordering steak at a steakhouse, and being non-confrontational, I laugh.

I start talking about music (a passion of mine). From previous conversations I know he’s not into music because I assume he doesn’t have a soul, so I bring up the topic if only to have something I can talk about. He hijacks the conversation by talking about being in marching band in high school and I let him because I’m so done with all of this. He leaves to use the restroom, and I catch the eye of the bartender. He winks again at me, I roll my eyes and smile.

As my mind drifts to the date I could have been on with the bartender, the waiter brings our food. Ben isn’t back yet from the bathroom, so like anyone with manners, I wait. It hasn’t been a minute since the waiter left and Ben is back in his seat. I make a comment referencing the Pulp Fiction scene where Mia Wallace says something about coming back to the table and having your food waiting for you. My quip falls on deaf ears because Ben is PISSED.

“Why do they do that? They can see that I’m not at the table. There’s no fucking reason why they can’t wait.” He goes on to say that no restaurant has old-fashioned service anymore, and that modern restaurants are the worst at this. I make a comment about how good his steak looks in an attempt to end this unnecessarily angry rant. I am ignored.

The food is mediocre at best and I’m really glad I’m not paying for it. Though I’m paying in a different way. When we finish, the waiter removes our plates and asks if we would like dessert. Ben interrupts my polite refusal with his own rather harsh one, and asks for the check. While we’re waiting he asks me if I drove here. I say no, that I took the train because it was easier than trying to find parking. I’m angry at myself for having the urge to validate anything I do to this asshole.

It’s now going on 11, and he asks me how much time I have before I need to get back to the train. I tell him I have about an hour, and he says that’s plenty of time to grab a drink at his favorite bar. I’m shocked that he wants to continue this, but I do notice that his tone is one of obligation. I get up to use the bathroom, and I notice he blatantly stares at my ass as I stand. I’m a mixture of annoyed and flattered. I end up taking pictures of the bathroom for my sister because we both dig hip bathrooms. Unfortunately the aesthetics are not conducive to snapping smartphone photos.

I don't want you to fight for my honor, I want you to act like we know each other.

I don’t want you to fight for my honor, I want you to act like we know each other.

When I get back to the table, Ben says he’s ready to go. I grab my coat and he’s already halfway to the door before I turn around. It’s shit like this that makes me hate dating. He’s complaining about service in the restaurant and he can’t even walk with me to the door. We do this follow-the-leader thing all the way to his car across the street. He unlocks my door and opens it, which frankly I’m shocked by.

I try making small talk and it’s effective, I even feel like he’s warming up a little. I wonder why I’m trying but I realize that maybe it’s me. I tend to be very standoffish and maybe my insecurities got the better of me. Maybe the bartender got the better of me. He drives way too fast while complaining about an accident he got into with a cab driver. I say something about him being a lawyer and being able to handle it and he lets out this weird laugh and says, “Believe me, I did.” Ben stops the car and gets out and I’m left wondering about some poor immigrant family who now owes him basically all their children.

He opens my door and we walk into this tiny dive bar. FINALLY. This…this is my kind of place. I’m a little ashamed at how overdressed we are but at this point I don’t care. He lets me order my own drink (gin and tonic, which I’ve never had before this night but it sounds cool) and he orders his (some sort of whiskey, or whisky, he makes a point of explaining the difference and I absolutely do not care). We talk a bit about the bar which is just really cool. It’s long and narrow, dirty, and has a bunch of Christmas lights everywhere. I start warming up to him again and he takes advantage of that by putting his hand on my knee.

“So, what’s your plan?” he asks, rather suddenly.

Confused, I start talking about my life plan, about how I should really get back into school and maybe move to the city or just start traveling. He removes his hand from my knee and I realize he meant my plan for the rest of the night. I pick up on these hints easily, and had he been as awesome as his emails had portrayed him, I’d probably be open to the idea of taking this back to his place. I laugh it off, and say that I should head back to meet my train.

As he drives me to the station, I grip the door handle out of sheer terror. He’s a terrible driver, and what’s worse is that he’s a very fast, terrible driver. This only solidifies my growing disdain for him. When the train station comes into view, I direct him to the closest entrance. A comment is made about living in the suburbs but I only half hear it because I am not dealing with this shit anymore. I thank him and give him a half-hearted hug. He leans over to do the same, but kisses me on the cheek instead. I’m caught off guard at how cold and slightly slimy his lips are; I stop myself from imagining what things would have been like if we did end up back at his place.

I shudder as I get out, thanking him again and he just nods, watching my ass. He continues to watch me walk to the door, but it’s locked. I turn around to him, thinking he’ll wait for me, but he waves and drives off. I’m left standing outside of the train station, in heels, at 12:30 at night. I walk around the block to the other entrance where a homeless guy holds the door open for me. He looks at me and says, “I saw that car drive off on you. Want me to fuck him up?” I smile and thank him with a $10 bill.

I never see Ben, or the bartender, again.


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