Questions From The Chase: Getting Back Into Dating

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This week’s question comes from some overachiever in med school. Question below.

This week I was asked on a date by someone of whom I’m acquainted with. I am in med school. Prior to starting med school, I was in a long term relationship with someone and we broke up right before I began. I haven’t been on a “date” in about a year. I have basically been covered up with relentless work during the week, however, love engaging in “The Chase” on the weekends. I am actually on a 2-weekend hot-streak, so-to-speak (humblebrag). Any pointers? Been out of the dating game for awhile.

Two-weekend heater huh? Nicely done. I wish I could say the same for myself, but I’ve been having some uncharacteristically bad luck lately. Getting back into the dating game isn’t easy. There are several things you need to be careful of when you’re dipping your toes back into the pool of singledom. If you can remember to do all of the things I’m about to tell you, I think you’re going to be fine.

First off, don’t talk about your ex. If the person you’re with broaches the topic of exes, fine. Give him/her a little information about your last significant other and leave it at that. Nothing turns a potentially good date to a crumbling ruin faster than some long diatribe about how your ex fucked you over or still tries to hit you up. You’d be surprised how little people give a shit about your past transgressions with an ex-beau. I’d relate it to a person telling you about your commute to work. People will politely pretend that they care, but once your ex comes into the conversation, most people’s brains are going on auto-pilot. Classic warning signs are going to be the person sitting across from starts saying “uh-huh” a lot and “oh, yeah, that sucks”.

If you’re going out to dinner, try for a place with a menu on the lighter side. I’m talking fish, sushi, farm-to-table bullshit. At least give off the impression that you don’t eat like a complete savage every night of the week. And don’t take that as me judging you if you do. I eat frozen chicken breasts, grilled cheese, or pasta most weeknights. But the last thing you want to be doing is farting all night from that cheeseburger you ate or having indigestion when after-dinner drinks are suggested a bar nearby. Keep it light and save the artery clogging for a late night out with your friends who don’t judge you.

This next point is important because I believe it’s a total myth that one person should be relied upon to keep up a conversation. Don’t feel like you have to fill silences with awkward laughter or generic topics like what you majored in during your undergrad years. Although I think it’s important to get a little background on the person you’re going out with, too much small talk about the weather, your long lost undergrad years, or traffic is going to make for a bad date. Believe it or not, there is such a thing as a comfortable silence. Sociopaths excluded, the person sitting across from you is more than likely just as nervous as you are to meet up. Which is why getting hella faded prior to a date is another big no-no.

Don’t get drunk or super high before showing up to the restaurant or bar where you’re meeting. Getting the munchies is fun, but stuffing your fat face with food while you’re trying to have a conversation is not. By all means, have a cocktail or a glass of red before you Uber to the rendezvous point, but don’t be slurring your words when you sit down and look this person in the eye. I once met up with a girl for dinner at 7 on a Friday night, and she showed up twenty minutes late bombed out of her gourd. She couldn’t string a sentence together and I ended up putting her in a cab ten minutes after meeting her. It was hilarious, but also terrible because I went home alone.

First dates are one big facade. Both parties are walking on eggshells trying not to do or say anything that will reveal how fucking weird they truly are. You’re probably going to tell some white lies about yourself. I do it all the time. Everyone does. Just make sure the lies are small enough that you can either remember to keep the lie up or, better yet, the lie is so insignificant that your date doesn’t even remember it.

You’re in med school, so I can’t imagine you have a ton of skeletons in your closet. Or maybe you do and all those schools that you interviewed with couldn’t find the dirt. Either way, keep it loose. Save the serious shit for the second or third date. The first date is an interview to decide if you want to see the person again. Worst case you have a few drinks and a nice meal and you never see him/her again. Plus, it’s always fun to laugh about bad dates you’ve been on. Everyone’s been on a few. But maybe the date goes well. Where do you go from there? Don’t feel like you have to bang on the first date. Get a goodnight kiss and get the hell out of there. Leave them wanting more. A little mystery is always good. Although I just remembered you telling me that you’re on a two-weekend hot streak. And everyone knows you never quit on a heater. A hot hand only stays hot for so long. Go big or go home. Good luck out there. .

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Johnny D

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