Dear Katy,

—Caffeinated and Crazy About Someone New

Illustration by Josh Zucker

Caffeinated,

Oh, this is so exciting! Your question (i.e., the knowledge that people my age still go on dates) has really restored my faith in college-age humanity. I may have just given away an integral flaw in my advice, in that I don’t often go on dates, but I think the best relationship advice always comes from the friends that absolutely don’t date. They’re the ones who get to observe the most crazy politics. The single ones just know more, or that’s what I’d like to think. Regardless, you have a date, and you’re going to absolutely kill it (with or without my help).
So, coffee shops are intimidating. I don’t think I’ve ever walked into a coffee shop and been like, “Yeah, I so belong here, I’m definitely cool enough for this, my grunge level for sure matches everyone else’s in the room.” Usually it goes something like this: “In and out Katy, in and out, put your head down, grab your coffee and run, or find a corner where you can blend,” or something similar and less panicky, but with the same amount of social anxiety. Probably along the lines of, “That kid in the purple shirt knows I’m a poser.” Most of the time, I think coffee shops are home-y and warm, but they’re also a place of judgment or posturing. That can be hard to handle, especially on a first date.

I’ve been on coffee shop dates before, and they’ve been fun. Usually I’ll have them with girls I just want to get to know better or friends who I love. Maybe these examples aren’t the same as a romantic date, but whatever—it can’t be that different. I still get nervous, I still want them to like me, I still worry about how I look and about what to talk about. In short, I have lived these struggles. I can give you a survival guide: Here is Katy’s Declassified—Heavily Specific—Date Survival Guide:

How Long to Expect to Be There:

You will be there for eons. Expect that. Prepare for that. If it’s a place like Kayak’s Coffee, you might even end up getting a meal, which is great! If it goes well, sometimes the date will advance to another venue. If I could give you a rough estimate, I would say anywhere from 1.5-3 hours. Your mouth will hurt from talking so much, and you’ll end up sipping on a lukewarm beverage, as you’ve been there for so long but somehow didn’t have enough time to sip the drink while it was hot. It never feels as long as it is though, especially if you stay for a while. You end up looking at your phone, laughing and going “Gosh, time flies when you’re having fun!”—or something equally cheesy.

What to Talk About:

Your absolute deepest, darkest, most embarrassing secrets. Just kidding, but they could come up! When you first get there, maybe bring up something you already have a little bit of rapport on or a common interest of which you’re already aware. If you get stuck, go for the basics: What are you studying? Where are you from? What do you do in your free time? Favorite book? Favorite movie? Now you might be thinking, “Katy, what are you doing? This is low hanging fruit. I want to impress this person, not make them think they’re in the midst of sorority recruitment.” And to that I would say, well, you’re right. Let’s crank it up a notch. Go for the “If you were stranded on an island…” questions, and the “So what’s your relationship with your parents like?” questions. Dig deep. Go all in. Insert more sports-like encouragement slogans here.

What to Wear:

What you feel comfortable in, but also what you feel confident in. I’m a huge outfit person and am the person who changes four times for no reason, so I’ve thought about these conundrums a lot. I believe, in terms of dates, that your outfit should reflect the interest you wish to convey. If you want to say, “I really, really like you, and I care about what you think of me,” maybe go for a nice skirt, dress or pants and blouse combination. If you want to say, “Here’s my style, now deal with it,” wear your most “you” outfit, in that it’s weird, unique and when people see you in it, they say, “That’s so you.” If you’re pretty comfortable with the whole interaction—and aren’t too afraid of how it’ll go or what they will think materially about you—go for something simple and just don’t worry about it.
Moral of the story is to be yourself. I know that sounds terrible, I’m sorry; I usually yell at people who tell me that. No one wants me to be myself, they want me to be who they want me to be: palpable, agreeable and sweet—not myself, which on any given day could be vastly different from that. But I think “be yourself” applies here. Y’all obviously like each other, and I think it’s important to present yourself as yourself. Maybe you clean up the edges and maybe you save some things for the next date, but you don’t lie. You don’t posture, and you make them feel like they don’t have to either. You’re going to talk a lot; it’s a coffee shop—it’s what people do. Just make sure that what you talk about—and what you say—represents you, unapologetically.
Good luck, my friend. You’re an inspiration to us all,
—Katy Hutson, Senior Scene Editor