I went speed dating

Breaking out of my comfort zone to get what I want

A few weeks ago, a friend sent me an Instagram DM. “Do you want to go??”

I followed the link of a drawing of a juicy ruby pomegranate to a post hyping up an IRL dating event from Hidden Gems. (Tagline: “Too precious for the apps.”) I’d seen flyers for their events at my gym, and I even knew a girl who had attended one and got a nice date out of it. Plus, anyone who knows me knows that I voraciously eat pomegranates come winter. So I took the inviting art as a sign.

“You know what…I’m down,” I wrote my friend back. I bought a $25 ticket and there was no looking back.

My commitment to putting more effort into dating IRL has been a slow burn this year. I’ve been on dating apps since I was 23, but I’ve never formed a real relationship from them, though I have dated a couple of guys for six months or so. (Writer

Shani Silver

has a lot to say about why you should delete dating apps for good, if you’re interested.) I met two past boyfriends at school, one in a bar, and one at a comedy show meant to hook up singles (I know, it’s a killer meet-cute).

I won’t waste a lot of time here talking about how soul-crushing and useless dating apps feel — if you know you know. But over the last couple of years I have used them less and less. I’m repelled by them, honestly — nowhere else in my life do I throw so much time and energy into an abyss with so little ROI. Putting my energy into talking to strangers online who generally don’t value me and don’t set a time to meet up 98% of the time feels extremely off-brand for me. Unaligned. Downright shitty sometimes. I don’t like hurting my own feelings, and dating apps began to feel like self-punishment.

But! I still want to date! And to successfully do that out in the world does feel so 2010, especially since the pandemic. People simply don’t talk to strangers anymore, even here in friendly ol’ Texas.

For a while, I tried to force myself to “be brave” and talk to an attractive man every time I went out. This is a good plan in theory, one that I still try to put into practice, but can also be too much self-pressure. It ends up feeling like another feeling-hurting exercise. If I didn’t work up the courage to talk to someone, I’d chastise and blame myself. I’d try to remind myself that the absolute worst thing someone can say is pretty much, “No, thank you,” but rejection can be a daunting thing, even when you’re leaning into it. (And I did get rejected sometimes, but every no leads to your next yes and blah blah blah.) And every now and then, the stars would align, and I would get a date out of my efforts. I cherished these small wins.

I decided that putting all of that pressure on myself to constantly be on and muster up the courage to talk to strangers wasn’t fair to me and put me into “hunt” mode when I’d rather focus on enjoying the moment and being present with my friends. But I also know that if I actually want a long-term relationship, which I do, it is my responsibility to go out there and get it. I’ll meet exactly zero potential boyfs while sitting alone in my home office, which is exactly where you can find me most of the time.

@jillathrillaLet’s talk about some of the downsides of WFH #grwm #therapy #dating #single #confidence #makeup #change #ootd #wfh #freelancelife #freelancer #remotework

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So I decided to try something different: IRL singles events.

At a dating event, everyone is there for the same reason: to find a date! You don’t have to worry if that cute guy by the bar is married or gay. All the men you can see until the Elephant Graveyard are also single and looking.

To test the waters, I attended Austin Monthly’s Singles in the City party back in February. (You can see what I wore and hear me talk about how I think WFH has affected my dating life in this TikTok.) This was an okay time!

jillathrilla

A post shared by @jillathrilla

Pros: There were a lot of attractive, normal men there (but more attractive, normal women, as is always the trend with these kinds of things because women are brave and go after what they want). Cons: It was a nightclub atmosphere, so the music was way too loud to have real conversations. There also weren’t any icebreakers, so it was 300 people just milling around with darting eyes, trying to find ways in to talk to cuties.

However, this is where I shine! I did go up to several different men I thought were cute, and two of them got my number. One never texted me—I see him regularly on my Lady Bird Lake walks, but we don’t speak. The other texted me but never asked me out.

This is where I get frustrated. We all paid money to go to this event. We got all gussied up. We spent time talking to each other. We already did all the hard parts! And now you’re not going to actually ask me out?!?

(And before you lecture me that women can ask out men too, I’ve done that a million times. I am in a place where I need my potential partner to take the lead, and I am leaning into that for now.)

Flash forward to May:

After a couple of very sad months spent grieving my grandfather, I am ready to seek joy in the world again. And I’m looking for a real love (or, at the very least, a summer love).

So, on Wednesday night, I put on one of my favorite first date dresses and drove to the function. We milled around upon arrival, decorating our name tags (I stuck a Lovers Tarot card on mine) and ordering glasses of wine. There were about 15 men and 25 women in attendance, mostly in their late 20s to late 30s. Then we all shuffled into the outdoor backyard where we sat four to a picnic table, two on one side who are interested in men, and two on the other side interested in women. We’d have about five minutes of conversation as a group (loved this — so much less pressure than 1-on-1 convos) inspired by a prompt (“Who do you feel most like yourself with?”) before two people rotated to the next table. So I met all my options within an hour, then we got to head back inside to talk more with people we found interesting.

I ended up staying until 11 p.m. and had four guys ask for my number. And the organizers connected me via email with a couple more guys who were mutually interested in me that I didn’t get a chance to chat with more before the night ended. Now that’s an ROI.

My speed dating lewk.

I loved that Hidden Gems brought together a diverse group of people from different professions, ethnicities, and even sexualities — certainly some people I wouldn’t meet in my usual social routines. The event didn’t discriminate by gender or sexuality, and there was a second speed dating round for those who identified as queer. I love the thrill of the unknown you get walking into an event like this — anything could happen! There’s a sense of adventure, and I left feeling a confident spark I’d never get from a lonely night of swiping.

My favorite part of speed dating was that the whole conceit seems to work! And not just for me personally—a couple I had seen talking when we first arrived were making out by a car at the end of the night. Inspiring!!

I had a conversation with one of the event founders that stuck with me. She basically said that while you might not be into every guy you meet at Hidden Gems (nor will you anywhere, of course), you’re going to get a quality group of men who are genuinely interested in dating and have taken a leap of faith to be here — just like you. It’s a whole world away from the “whatever, who cares” attitude of Tinder et al.

So, in conclusion, I’d go speed dating again! In fact, I will go again. My local Alamo movie theater runs a monthly “We Met at Alamo” event for “sociable singles” — I poked my head into the bar area while it was going on the last time I was there and it looked like a good time. I’m ready to find a boo to enjoy my Alamo pass with in the A/C all summer long.

As an IRL dating bonus, I went on a fun first date this weekend with someone I met while I was out on the town last weekend! We took photo booth pictures of us smiling and kissing, and instead of tucking them away, I put them up on the fridge. They’re a reminder to myself of hope, possibility, joy, and the goodness that often comes when I step outside my comfort zone — a gift from me to me.

Trying new things and breaking free from routine isn’t just good for my dating life; it’s good for my creative life too. Here are a few of the other new things I’ve been trying over the last 6+ months to ignite my soul and find new ideas:

• Committing to completing every day of 1000 Words of Summer. Today is day four! I used days one and two to work on a novel idea that’s been bouncing around my head for years, and yesterday I wrote this newsletter.

• Making the new iteration of the CSBC podcast and recording solo episodes (launching June 27!). I’m learning how to be more of my authentic self behind the mic and how to talk about topics I’m interested in without feeling like I have to over-prepare. I’m having a lot fun!

• Painting classes at Laguna Gloria! I’ve taken a watercolor 101 and acrylics 101 class and loved both. I’ve told myself the story that I’m a “bad” artist since childhood, and I’m reclaiming that creative spark now.

• Attending a lot more networking dinners and events locally. This has resulted in many business leads and a couple new clients.

• Wearing my curly hair natural and learning how to better care for and style it (and unlearning the hegemony of straight hair)

• Going new kinds of places alone. (And also not forcing myself to go somewhere alone if I just don’t feel like it.)