By Jonquilyn Hill
If you want to hear someone complain, ask a single friend what dating looks like right now. You’ll likely hear about first dates that go nowhere, conversations that read like social media posts, and many people deciding to accept single life. What once felt like an endless stream of romantic possibility — especially through apps — now feels stalled.
“Dating can be so exhausting, depleting, demoralizing, and I only think dating apps have increased that experience for single folks,” says dating coach Lily Womble. Despite how discouraging it can be, many people still want partnership.
Womble, author of Thank You, More Please: A Feminist Guide to Breaking Dumb Dating Rules and Finding Love, spoke with Vox about how to move past dating fatigue. “If you do want to find love in a romantic partnership, there is a more healthful and empowering way to go about it that centers you as the main character,” she explains.
How do you center yourself and move your love life off the phone and into the real world? That’s the topic of a recent episode of Explain It to Me, Vox’s weekly call-in podcast. Below is an edited excerpt of my conversation with Womble. You can listen to the full episode on Apple Podcasts, Spotify, or wherever you get podcasts. To submit a question, email askvox@vox.com or call 1-800-618-8545.
If you’re used to dating apps and you want to meet someone in person, how do you make that happen?
Dating in person has become a rarer social skill. Womble says our reliance on apps has harmed how we connect: the apps are built like slot machines, keeping people scrolling and hoping for a hit. She recommends resetting your brain away from apps and getting back to in-person connection through a three-step approach.
What are the steps?
First: joy-building. Joy creates connection. Leave your house, get off the couch, and do something in your town or city that brings you joy alongside other people. It can be free or paid — the aim isn’t to be near attractive people, it’s to form new friendships and expand your social circle. That expansion plays the same role as an app: it widens the opportunity window to meet someone.
Womble says joy-building can lead to unexpected introductions. “You never know which 70-year-old you meet at your quilting night in your small town, whose son’s boyfriend’s cousin comes to a party and suddenly you’ve met the love of your life.” She shares her own example: she met her husband after taking an improv class, making a friend who introduced her to a social circle, and then meeting Chris.
Second: co-conspiratorship. Ask friends to help more intentionally. If a friend says they don’t know any single people, propose co-creating solutions: have them keep an eye out at their workplace or events, and tell them the kind of person you’re looking for and the questions to ask.
Womble gives a client example: two people became each other’s co-conspirators across different states. One visited the other, met a man at the airport, asked qualifying and disqualifying questions, learned he was single and a good fit, and set them up — and they started dating. Friends can support you the way you support them.
Third: flirting. Womble admits flirting can feel “the most vomitous, nerve-wracking part” but emphasizes it’s a learnable skill, not an innate gift. She defines flirting as a joyful, courageous connection: approaching someone, asking a genuine question, and seeing if they want to co-create a conversation. To test romantic interest, she suggests simply asking, “Hey, random question. So are you single?”
Flirting often requires “10 seconds of courage,” she says — for example, going up and saying, “Hey, you’re cute. I just wanted to come tell you that.” Womble recalls a client who did that on a crosswalk and later dated the person she approached.
You make it sound easy, but getting out, being joyful, and talking to people can be hard. Many people are shy, and some lost social practice during the pandemic. How do you handle that?
Womble notes we missed social reps during lockdowns, especially Gen Z. She recommends a rejection-resilience plan stored in your phone’s notes app: decide how you’ll be courageous and how you’ll care for yourself after a hard moment. Not everyone will welcome your approach — some people are uncomfortable or uninterested — so prepare for rejection with self-compassion strategies.
“It’s as simple as understanding that your brain’s going to think it’s dying after an experience of rejection. Just say, ‘I think I’m going to die after rejection. It’s a thought, not a fact.’ Then have a plan to be compassionate towards yourself,” she says, noting self-compassion is science-backed and can lower cortisol and boost resilience.
She also recommends a flirting ladder to build distress tolerance.
How does that work?
Begin with a tiny, concrete step: make one second of eye contact, then look away. That’s level one. Next, hold eye contact for three seconds. Build in small steps to expand your distress tolerance. If you’ve never made eye contact with a stranger or said hello, write five simple actions to try this week: eye contact, saying hello, and so on — one client even tried a “wink and run.”
Planning short, time-boxed acts of courage — “I’ll do this for 10 seconds and then I can bail” — makes it easier to act. Over time, those small steps increase connections in your life and raise the chances of meeting the right person.
Source: vox.com
