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Ask Anna: What to do when you’ve been dating but aren’t ‘official’

September 12, 2025 by Chicago Tribune

Dear Anna,

I’m a 28-year-old woman who’s been seeing this amazing guy (31) for eight months now. We spend most weekends together, text daily and I’ve met some of his friends, but we’ve never actually had “the talk” about what we are. I’m pretty sure he’s not seeing anyone else because we’re together so much, and I’m pretty sure he knows I’m not either, but neither of us has said the words “boyfriend/girlfriend” or “exclusive.” My friends think eight months is way too long to go without defining things, and honestly, I’m starting to feel weird introducing him as “the guy I’m dating” when it feels like so much more than that. I want to bring it up, but every time I think about it, I worry I’ll come across as clingy or like I’m trying to pressure him into something he’s not ready for. He seems happy with how things are, and I don’t want to rock the boat and potentially ruin what we have. But at the same time, I feel like I’m in relationship limbo, and it’s starting to make me anxious. How do I have this conversation without seeming desperate or needy? And is eight months really as long as my friends are making it seem? — Stuck At Gray Area

Dear SAGA,

First, let’s clear something up: You ARE in a relationship. You’re texting daily, spending weekends together and meeting each other’s friends. The only thing missing is the “label,” which you get to decide if that’s important to you or not. (It seems like it is.)

Your friends are right that eight months is a long time to exist in this undefined space, but here’s the thing — you’re not “desperate” or “needy” for wanting clarity about something that’s taking up significant emotional real estate in your life. You’re a functioning adult who deserves to know where she stands. Not to compare your love life to capitalism, but imagine if your job told you after eight months, “We love having you here, but we’re not ready to discuss your title or benefits yet.” You’d polish up that resume, right?

The fear of seeming clingy is doing you no favors here. It’s keeping you trapped in an anxiety-inducing limbo when a simple conversation could set you free. And honestly, if asking “What are we?” after eight months of consistent dating scares him off, then he wasn’t as invested as you thought anyway. Better to know now than at month 16 or 36.

Here’s your action plan: Stop overthinking and just ask him to go steady already. You can be cute about it, if you want, and show up with a cake that says “Everything’s batter with you. Be my boyfriend?” or slip him a note like you’re in seventh grade.* Or you can be direct: “Hey, I’d like to call you my boyfriend. What do you think?”

But here’s where it gets fun. Don’t just ask for the title and call it done. Use this as an opportunity to actually discuss what being boyfriend/girlfriend means to both of you. Does it mean you’re each other’s plus-one to office karaoke night? Are you spending holidays together? (Or at the least discussing plans with each other first, even if you do things separately?) Does he get a key to your place? Is he expected at your cousin’s wedding in six months? Does he get your Disney+ password??? These conversations are way more interesting and useful than just slapping labels on things.

Think of it as relationship logistics mixed with a getting-to-know-you session. You might discover he thinks boyfriends should text good morning every day, while you think that’s clingy. Or maybe you assume girlfriends get priority on Saturday nights, but he’s been planning guys’ trips without considering you. Better to hash this out now than three months from now when you’re fighting about why he didn’t invite you to his friend’s birthday party.

Remember, a guy who’s genuinely into you won’t be frightened by your desire for clarity. Many people (especially men) assume things are fine as long as no one’s complaining. He might not even realize you need this conversation.

And if he’s not ready for labels? That’s valuable information too. You can decide if you’re comfortable continuing as-is or if you need something more defined. Either way, you’ll stop living in relationship purgatory.

Your anxiety is trying to protect you from rejection, but it’s also protecting you from the relationship security you actually want. Trust that you’re worth a clear answer, because you absolutely are.

The boat is a lot sturdier than you think,

Anna

———

*Ooh, or make an official-looking document that looks like an overdue bill from the Department of Romantic Affairs that’s like, “We’ve waited long enough, Steve!”

___

(Anna Pulley is a syndicated Tribune Content Agency columnist answering reader questions about love, sex and dating. Send your questions via email (anonymity guaranteed) to redeyedating@gmail.com, sign up for her infrequent (yet amazing) newsletter or check out her books!)

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