dating, winery

dating, winery

As a well seasoned singleton, I've found myself in a fair range of dating scenarios over the years. I've been asked out at music festivals, Halloween parties, asked out by baristas, set-up by friends, approached at bars, approached out on the street, asked out by a drunken friend who didn't remember it by morning, asked via dating apps, and even had a guy slip me his number on a napkin once when my date was in the bathroom (bold move, but I never call him). The one thing all these situations have in common? I was asked out by the guy.

I was swiping though profiles on OkCupid when a little pop-up about women making the first moved showed up in my feed (OkCupid includes all these little fun facts and tips as you swipe). It hit me that in all my past relationships and dates, I've almost always* waited for the guy to make the first move. How many opportunities had past and how much time had I wasted over the years because I refused to make the first move? Subtly—or not so subtly—dropping hints, just waiting on a guy. Sometimes it felt like I was doing everything short of standing with a big, blinking neon sign: "Hey! I like you!" Yet in none of these situations did I ever speak up. Why? Because it's more traditional to let the guy ask you out?  I've never let being a girl stop me from doing anything else I wanted, so why let it stop me from asking a guy out?

oregon, wine, gretchen holzgang

oregon, wine, gretchen holzgang

So I made my first move.

I use to have a go-to move on Tinder when I wanted to keep the conversation going but didn't want to ask something stupidly generic: I'd tell a joke. (My favorite "There are two fish in a tank, one turns to the other and says, 'Do you know how to drive this thing?'" was usually where I'd start because it's short and puny and easy to write out in a single message.) But if I was going to actual make the first move on someone I felt like it should be saying something a little more thoughtful than a pun I could just copy and pasted to literally anyone.

When I decided to change my dating approach and reach out first, I already had someone in particular in mind. Unlike dating apps that are generally photo-centric with less detailed profiles, OkCupid is full of people with longer, more in-depth profiles. This has totally changed the dating app experience for me: While a photo can grab my attention, someone's personality is what I tend to fall for. That sounds dorky but I promise it's true; profiles generally sway me way more than photos. I never make the first move simply because someone is attractive or has red hair (not that those things don't help... god help me and those red heads). It's usually something they write that gives me the feeling that this is someone I'd like to know. In my first foray into making the first move (surprisingly not on a red head), I did something I've never done before: I opened with a super embarrassing story about myself (without going into particulars, you'll just have to trust me when I say it went along with something he'd written in his profile). I drafted my idea, triple checked it for typos, sent it off, and waited.

Waiting for someone to reply is the hardest part. There's a limbo-like feeling to it that I simply don't enjoy. However, since I've decided to put more effort into making the first move, only once has the person never replied—and I can't even remember who that person is without going through my message archive. Over the past few months I've also noticed something else interesting: most of the best interactions I've had on a dating app have been with guys where I started the conversation. In other words, the rejection is pretty easy to shake off while the payoff has been worth what is, in reality, a fairly minimal investment.

Making the first move on a dating app, though, is easy compared to doing it in person. Rejection across a phone screen with someone you don't really know feels substantially less daunting. I had a writing teacher in college who had worked as an actress in Hollywood before getting into writing and she summarizes the difference between online rejection and in-person rejection perfectly: It's a hell of a lot nicer to get rejected in the comfort of your own home while wearing PJs than having to get all dressed up and go out to get rejected. I've experienced plenty of in-person rejection (enough that it probably warrants a post of it's own). Getting rejected in person—whether through a breakup or an unrequited love interest—can be flat out painful. But in my experience it's nothing that you can't bounce back from. In the end, I'd rather risk the hurt of rejection then to spend my life always wondering "what if?"

*There are actually two times on record where I made the first move in person: The first when I gave my number to a cute guy I saw alone at the bar. It turned out he was in a relationship already but he was super nice about it, so I still consider it a positive experience. For me, it was more about having confidence to do something kind of scary and have everything be alright. The second, was at a party when I handed my phone to a guy I'd been talking to and said "I'm leaving," indicating that he should put his number in my phone for me (I'm generally never that bold). He put it in as "captain" and we started dating a few weeks later. To this day that's still how his number is listed in my address book.