Q:
Okay, so I’m going into my first year of college this fall and I’ve still never been on a real date. Sure the pandemic played a big part in that, but I always feel like I’m behind somehow when my straight friends or heck, even my other lesbian friends talk about flirting, dating, and sex. It’s not that I don’t want to date someone, it just never seemed to happen for me so I didn’t force it. I would flirt with girls occasionally but it always fell off after a couple conversations so I just let it go. But now, there is this girl who I really want to get past the talking stage with, she’s super sweet, hot, and funny. She even remembered my order at the place she works after just one visit. So now I’m stuck, I want this to go somewhere but I genuinely don’t know how to flirt or initiate conversation without being super awkward, any help would be much appreciated. ——MM
A:
Hi, MM! Your letter is really relatable — all of us have been there at one point or another! First off, congratulations on having a real crush. Regardless of what ends up happening, crushes can be SO fun. Getting past the talking stage can feel kind of insurmountable, but I promise you it’s not. There are a few moving parts here, so I’ll jump right in.
College isn’t a deadline.
I don’t know if this is happening for you, but I think that the start of college can feel like a deadline, of sorts — it can be really easy to feel like we shouldn’t go off to college without having done certain things, like date, first. Maybe it’s because going off to college gets painted as a kind of ending in a lot of pop culture. I’m wondering if this might be where some of your sense of urgency is coming from. The great news, though, is that going into your first year of college is actually a beginning! Whether you’re headed somewhere new or staying in your hometown, when classes start, you’ll be meeting a ton of new people and new activities, and your opportunities to socialize, flirt, and date will open up exponentially (yes, even in the continuing pandemic). You’re going to be learning new things, talking about them with new people, and a bunch of those people will be single and some of them will be super cute and not one single person you meet will know (or care, if you get to know someone and want to tell them) how much dating experience you had in high school.
A note about workplaces
From what you wrote, I couldn’t tell whether or not you know your crush from outside of the place where they remembered your order. You can definitely chat with them either way, but if you only know them from their workplace, there will be a few things to keep in mind.
This was a few years back now, but have you ever seen the music video for Mary Lambert’s song She Keeps Me Warm? The video tells the (absolutely adorable) story of Mary meeting someone cute at the cafe she frequents. In the video, Mary and the person who works at the cafe start having friendly conversations. Eventually, Mary “forgets” her book at the cafe — and the person who works there returns it with their own phone number tucked inside. (Of course, we’re not all in a music video, and things don’t always work out that sweetly, but we can dream!) The point is that you can definitely try to get to know this person better, but make sure they take the lead on anything besides conversation, and can walk away if and when they want. As you chat with them, make plenty of space for them to signal their interest, or not (and being nice to you, or remembering your order, doesn’t always signal interest in and of itself, since that’s essentially part of their job). Space and agency are always important, but they’re particularly important when a person is at their workplace. And this leads me to an important point:
Flirting is a conversation.
Okay, so you’ve met someone who is sweet, hot, and funny! You’ve spoken to them! Congratulations! Getting to know them better — and flirting with them — is going to look a lot like continuing those conversations. The big secret about flirting is that it has a lot in common with… enthusiastically getting to know somebody. It’s just a little bit zestier. Flirting involves a lot of asking them questions about their life and being really interested in the answers, sharing pieces of your own life with them, everything you would do if you were getting to know a new friend. Which you are! If you’re feeling awkward, asking them a question about themselves that lets them talk freely will help. The more you can focus on the experience of getting to know the person, and really listen, instead of worrying about what might happen next, the better things will go. But speaking of what might happen next…
In order to date someone, you’re probably going to have to ask them out.
I spent a lot of time in my twenties waiting to be asked out by the people who I wished would ask me out (specifically, any queer person, instead of the straight men who tended to ask me out) and it never happened. I truly wish that someone had pulled me aside and explained that people aren’t mind readers, and in order to date the people I wanted to date, I was often going to have to make myself vulnerable and ask those people out! It was a memo I didn’t get until I turned 30, came out to my family and friends, and started learning to ask for the things I wanted in my life. The first time I asked someone out, it was online, after chatting a bit on a dating site, and I was petrified. The second time I asked someone out, it was in person, after getting to know them pretty well as friends, and THAT terrified me even more. I have never had a more out-of-body experience than when I told that second person, as we walked to our cars after a night at our town’s little part-time queer bar, “hey, I have a crush on you.” But I did it! And it worked out. Telling people what you want, directly and clearly, with space for them to answer honestly? It’s sexy, it’s confident, and most importantly, it’s useful. It gets easier with practice, too — I promise.
As I write this, students are once again flooding my college hometown, moving into the dorms, getting ready for classes to start. Soon you’ll be doing the same thing! [Editor’s note: We’re publishing this a few weeks after Darcy originally wrote it, so it’s possible you’ve been at college for almost a month now! Thank you for being patient with our response time!] You’re going to have a great time in college, and there will be SO many opportunities to practice flirting, to ask people out, to kiss the girls you want to kiss. It’s gonna be great, I promise. 💙
You can chime in with your advice in the comments and submit your own questions any time.
“In order to date someone, you’re probably going to have to ask them out.”
I really don’t have anything to add to this lovely advice.
Oh, except that I do. And that is that it is OK to be awkward when initiating flirting or asking someone out. It’s kind of unavoidable so just own it and be your best awkward, adorkable self.
oh yes, awkward is adorable!!
I often remind myself of Brené Brown’s motto: awkward, brave and kind. It has served me well!
As a 30-year-old who’s been in the dating game for over a decade, I still really needed to hear this advice –
“Telling people what you want, directly and clearly, with space for them to answer honestly? It’s sexy, it’s confident, and most importantly, it’s useful. It gets easier with practice, too — I promise.”