Did you swipe right on Tinder this weekend with your newest future love? Did you give your number to the hot guy by the lemons at Mariano’s? Or finally build up the courage to ask out your college crush after taking an Ambien? (This may or may not have happened to me.) Well, get prepared for your date this weekend by reading the following rules and tips for securing a second date in Chicago. Avoid these first-date faux pas and you'll be fine.
Get on the calendar: People in Chicago are busy. There is nothing worse than the non-committal, “Let’s hang this weekend.” Dude, I need a date, place, and time. A text like: “Hey! Not to bother you—I know you’re busy, but let me know if you’re free this weekend. I seem to be popular this weekend, but you’re first in line. Ha ha” Really means: “Umm you said you’d call me to do something this weekend and it’s Thursday and I have yet to hear from you. WTF? I do have other friends who are asking me to do all sorts of things and I can’t wait for you to get your shit together and call me. Thanks.” I have other things going on and if you want to get on my calendar, you better do it now. I promise you, marriages start with a locked-in date, place and time.
Do not insist he or she comes to your neighborhood: You live in Rogers Park and he’s in Pilsen? Meet in Lakeview. Halfway is appropriate. Find a place that is easily accessible for both of you to get to, ideally involving no more than one CTA transfer. A majority of Chicagoans do not have a car, so if you’re really feeling generous, send an Uber for your date and you’ll definitely get a second one. (But really, just avoid dating anyone who is not on the same El line as you. You may as well give it up now. Seriously, Rogers Park is really far.)
Don’t choose somewhere super expensive: Once, a dude told me the only place he would go in Wicker Park, our halfway neighborhood, was The Violet Hour. Even if you’re paying, you look like a douche by claiming that you'll only go to one expensive spot. You do not know how much people make, and dating gets expensive. Choose your first date place with a low key and relatively affordable option. It doesn't have to be a dive bar, but maybe somewhere with $13 cocktails is not the best first date locale. (Unless you’re rich. I don’t know what that’s like.)
Please no homophobia/sexism/racism: Okay, while I should not have to say this, this is an issue. I was recently on a date in a lovely wine place where there was a painting of two people kissing. My date asked me, “Is that two guys kissing?!” First, the painting looked very gender neutral, and secondly, who cares? I realize this did not make him a raging homophobe, but it was definitely an ignorant comment that turned me off. If you’re homophobic, racist or sexist, please look at your life and change that. Even if you're not, please think before you speak. This is an impression that people do not find attractive.
Do not go to a 4am bar: Nothing says romance like making out in the corner booth in The Continental at last call. I wish I could say I’ve never done this. I mean, I haven’t…in 2015. But if you’re at a 4am bar this means that it is probably not going to be serious. Not looking for serious? Fine, take her or him to a light night spot and carry on.
Never, I repeat, never leave your date on the corner to get home alone: Make sure there is an Uber, a cab, a bus or a train and your date is on or in it. While I try to make these all gender neutral, please do not leave a woman on a scary corner and wish her luck in getting home. Even if you never have to see her again, please make sure she’s okay. This has happened to me more than I could ever have anticipated. Even if you're Common, I guarantee that you won't have a second date with a woman if you leave her at the corner of Damen and Milwaukee at any time of the evening.
I am not responsible for any personal items lost or stolen on this date: Date goes well, huh? If you find yourself lucky enough to be making the bus ride home in the morning, do not leave any personal items. I swear people do this on purpose to see you again. And even if you didn’t do it on purpose, it makes it look like you did. A guy left his iPhone in my bed once. Even if I didn’t ever want to see him again, I had to. A guy held a pair of earrings hostage for a year and would randomly text, “You want your earrings back?” in the wee hours of the morning. I certainly did not need my $10 earrings back that badly.
Do not overstay your welcome: Spent the night? Do not hang out the entire next day. Thank the person, take all your stuff (see above) and make your way home. The day after a night out, all I want to do is watch Friends and eat peanut butter out of the jar, and I cannot do that if you are still here from our date the night before. Please make a graceful exit and set a time, date and place to see him or her again.