Ask Anna: Situationship detox - learning to date for real

Dear Anna,

I'm 28 and for the past few years, I've been fully committed to the casual hookup lifestyle. I'm bisexual and I've had a string of no-strings-attached situationships with people I met on apps - probably a dozen or so in the last two years alone. I was totally fine with it. I wasn't looking for anything serious, and honestly, I was part of the problem - I kept things surface-level, avoided emotional intimacy and bailed the moment anyone caught feelings. But about a month ago, I met someone at a friend's birthday party who's completely different from my usual type.

They're thoughtful and funny and genuinely interested in my life. We've been hanging out regularly, and it's not just hookups - we cook dinner together, we go for walks, they texted me a song that reminded them of me. Last week they brought over homemade cookies because they remembered I mentioned loving snickerdoodles. I think I actually like them, and that's terrifying. I've spent so long keeping people at arm's length that I don't even know how to do this anymore. How do I break out of the casual-only mindset and let myself be vulnerable with someone? What does healthy dating even look like when you've been operating in no-strings mode for years? - Scared of Something Real

Dear SSR,

First of all, congratulations on meeting someone who makes you want to try. That's huge, and the fact that you're even asking this question means you're already halfway there.

Here's the thing about spending years in casual-only mode: It's fun, yes - assuming mutual consent, honesty and integrity - but it can also be a protective strategy. You keep things shallow so you don't have to risk getting hurt. You control the narrative by staying emotionally unavailable. It works great until you meet someone you actually want to let in, and then suddenly all that armor feels really heavy and you don't know how to take it off.

The good news is that you're already doing the work. Homemade cookies, thoughtful texts, actual conversations - you're allowing this person to care about you in small ways, and you're noticing it instead of running. That's progress.

Keep it up by being honest about where you're at. You don't have to have a big dramatic "I've been emotionally unavailable for years" confession, but you can say something like, "I really like spending time with you, and I haven't felt this way about someone in a long time. I'm a little out of practice with the whole intentional dating thing, so bear with me." Vulnerability goes a long way toward trust and it doesn't have to be a grand gesture - it can be as simple as admitting you're nervous.

Next, reframe what intimacy means. You've been operating in a world where intimacy equals sex and nothing more. But real intimacy is showing up consistently, sharing parts of yourself that aren't just physical, letting someone see you when you're not at your best, and so on. It's texting them about your day. It's asking about theirs and actually caring about the answer. It's making plans more than 24 hours in advance. These things might feel awkward or overly earnest at first because you're not used to them, but lean into that discomfort. That's where the growth happens.

Something else to think about - start to notice your patterns. When things start feeling too real, what do you usually do? Pull back? Pick a fight? Ghost? Start paying attention when those impulses kick in, and instead of acting on them immediately, pause. Ask yourself: Am I actually upset, or am I just scared of getting close? Sometimes just naming the fear is enough to keep you from sabotaging something good.

You seem to be doing a good job receiving care from this new person, so keep that up. Sometimes, when we've been casual and surface-level for a long time, when someone does something genuinely sweet - like bringing you cookies or remembering something you said - your instinct might be to deflect or minimize it. Don't. Just say thank you. Let it land. Let yourself feel cared for without immediately trying to even the score or prove you don't need it.

Lastly, accept that you will mess up because you're human and we all do. It's OK. And it's part of building something lasting. You're going to have moments where you revert to old patterns - where you pull away or say something dismissive or try to keep things light when they're getting real. That's OK. You're relearning a new skill. The key is to notice when it happens, apologize if you need to, and keep trying.

And here's the most important thing: being vulnerable and letting someone care about you doesn't make you weak or needy. It makes you a person fully alive in the world. You've spent years protecting yourself, and that served a purpose. But now you've met someone worth risking something for. Open yourself to it.

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This story was originally published May 7, 2026 at 4:39 AM.