Ask Anna: Dating with confidence after a long break
I recently got out of a long-term relationship — seven years, monogamous, talked-about-getting-married serious. I'm 34, and this is the first time I've been properly single since my mid-20s. It's been a mix of freeing and terrifying. The dating scene feels like a completely different planet now — apps, situationships, ghosting, all of it. I'm trying to stay open and curious, but sometimes I feel like I'm playing a game where I don't know the rules. More than that, I'm worried about losing myself in the process. I spent so long being part of a couple that I'm not sure how to fully show up as just … me. How do I start dating again in a way that's authentic and grounded, without becoming jaded or overwhelmed?
Dear NOOB,
First of all — welcome. Not just to the dating scene, but to the strange and exhilarating territory of rediscovering yourself. The former may provide you with unsolicited dick pics and beer-and-queso-dip dinners, but the latter? That's worth the hullabaloo.
Coming out of a seven-year relationship is no small thing. That's not just one chapter closing — it's an entire volume. And now you're standing at the start of a fresh one, page blank and terrifying, wondering what the hell comes next. Totally normal. Totally brave.
Let's talk about that fear of losing yourself. I want to offer a reframe: You're not losing anything — you're yourself. After years of being 'we,' you're learning how to flip that first letter upside-down and be 'me' again.
The good news is you've been you all along, so it won't be impossible. Indeed, it should be . Even the most independent among us tend to lose a little of ourselves when we boo up, and getting back into the things we loved is maybe the best part of being single after a long period of togetherness. And getting back in touch with you is the most important thing you can do before trying to build anything new with someone else.
Dating doesn't have to be an endless mess of swipes and disappearing acts. Yes, the modern scene can be absurd ('being chill' is not a hobby!), but it's also filled with people just like you — figuring it out, craving connection, hoping to be seen. Finding them may be something of a chore, but a worthwhile one.
Here's what I suggest:
Start with clarity. Before jumping in, ask yourself what you really really want. Not forever — just for now. Make a list. Start wild and a little absurd. (You can always edit it down later.) Are you craving flirtation? Adventure? A future partner? Orgasms? Something in between? Do you want to visit every BBQ restaurant in your area? Do you want to meet people completely outside your usual type? Do you want dates that last no more than 30 minutes, once a month? Getting clear on your own desires will help keep you from getting swept into someone else's and can help with the deluge of choices on apps. Someone might be a 'maybe' until you realize you're after completely different things, then get shunted to the 'no' column. You don't have to declare your every want on your dating profile in neon lights, but knowing it for yourself will help you make better choices.
Treat dating like a big experiment. Because it is. (So is life!) Despite what reality TV tells us, you are not auditioning for love. You are observing, gathering data and learning what feels good — and what doesn't. Every date doesn't need to end in fireworks — sometimes, it's just lunch and learning that you can't stand people who brag about their crypto gains. That's still useful intel.
Reconnect with your 'you-ness.' Outside of the apps, this is your time to take up space, and to rediscover what lights you up. Try things solo. Join a pottery class, go to a trivia night, take a weekend trip. The more grounded you are in your own company, the easier it is to spot people who complement rather than complete you — or worse, drain you.
Protect your hope. Dating can be disheartening, yes. So take breaks and breathers. Don't let the cynicism of the internet rob you of your softness. Keep your heart open, but don't hand it over for free. Let people earn your time and tenderness. You've spent years learning how to love someone deeply — now, learn how to love wisely.
Stay rooted in who you are becoming. Play the long game. You don't have to rush. You don't have to perform. There's power in pacing yourself. As the poet Nayyirah Waheed wrote,
So take your time. Stay curious. Do things that scare you a little. And above all, be kind to yourself. The right people will love that you've done the work to know who you are.
Welcome back to you.
———
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