14 Awkward Signs Someone Has Been Out Of The Dating Game For Way Too Long

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Most people don’t stay in the dating game long-term without taking any breaks.

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Either they end up in relationships or they decide to be on their own for a while, both of which are totally valid. However, as with anything, when you’re out of practice for so long, things can be a bit awkward when you dive back in. Here are some signs someone hasn’t been actively dating for a while, and it might take them a while to get back into the swing of things.

1. They don’t know where to meet people anymore.

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If someone’s been out of the dating scene for a while, they might be unsure where people even go to meet these days. With everything shifting online, it’s easy to feel lost if you’ve been away from it all. They might ask friends for tips or try every new app without much success. The landscape has changed, and finding a rhythm again can be tricky. It’s all about figuring out what feels natural these days.

2. They forget how to flirt.

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Flirting can feel like a distant memory after a long dating hiatus. Someone who’s rusty might struggle to come up with anything other than polite small talk. They’re used to conversations staying in the safe zone, so turning up the charm feels foreign. It’s not that they can’t flirt; they’re just out of practice. It takes time to get back into the playful side of things.

3. They dress like it’s a different decade.

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Someone who hasn’t dated in a while might have an outdated style that doesn’t quite match today’s trends. They’re comfortable in what they’ve always worn, but dating brings a whole new level of self-consciousness. Updating their wardrobe might feel like a big step, but it can give them a boost. Dressing for today’s scene doesn’t mean losing their own style; it just means finding something that fits the moment. It’s about feeling good and confident in their own skin.

4. They overshare right away.

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When someone hasn’t dated in a while, they might forget that sharing everything on a first date isn’t the best move. They’re excited to connect and may go a bit overboard with personal details. It can catch their date off guard and even feel overwhelming. Learning to pace a conversation is part of getting comfortable again. A little mystery never hurts in the early stages.

5. They struggle with basic dating etiquette.

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Dating etiquette changes over time, and if someone’s been out of the game, they might be out of touch with the basics. Whether it’s who pays, how to follow up, or even how long to wait to text back, these things can feel like a puzzle. They’re not trying to be awkward; they just don’t know the current “rules.” Getting back into it takes some adjustment. Etiquette is simpler once they start feeling things out naturally again.

6. They hesitate to make the first move.

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Someone who hasn’t dated in a while might feel nervous about making the first move, whether that’s suggesting a second date or going in for a kiss. They’re unsure of the signals and don’t want to risk making things awkward. Overthinking takes over, and suddenly, they’re stuck in a waiting game. Taking a small chance can help them break the cycle of hesitation. Sometimes, it’s just about testing the waters and seeing where it goes.

7. They talk about exes too much.

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After a break from dating, it can be easy to let conversations slip back to familiar territory, like past relationships. They might bring up exes as a reference point or comparison, not realising it sounds like they’re still hung up. It’s natural to reflect on the past, but bringing it into new dates can be off-putting. Focusing on the present helps make new connections feel fresh. It’s a chance to start with a clean slate.

8. They’re unsure how to handle compliments.

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Receiving a compliment can catch them off guard if they haven’t dated in a while. They might brush it off or laugh it away, feeling a bit awkward about the attention. It’s not that they don’t appreciate it; they’re just not used to it. Accepting compliments gracefully can take some getting used to. Sometimes, a simple “thank you” does the trick and keeps the moment light.

9. They text like it’s an interview.

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After a dating break, texting can feel like a formal exchange rather than a relaxed conversation. Someone might focus on getting to know every detail about their date, making it feel more like an interview than a chat. This approach can feel stiff, even if their intentions are good. Loosening up in texts can make things feel more natural. A bit of casual back-and-forth helps bring out real connection.

10. They don’t know how to end a date.

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Knowing when and how to wrap up a date smoothly can be tricky for anyone out of practice. They might linger awkwardly or feel unsure whether to go for a hug, handshake, or just say goodbye. This hesitation isn’t a lack of interest—it’s just rustiness. A simple, genuine goodbye can often make things feel comfortable. They’ll find their rhythm with a bit more practice.

11. They rely on clichés.

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When someone’s been out of dating for a while, they might fall back on classic phrases or clichés without realising it. Things like “So, tell me about yourself” or “What do you do for fun?” can come off as rehearsed. While they’re just trying to make conversation, relying on the usual lines can feel stale. Fresh, genuine questions make things more interesting for both sides. It helps the date feel more like an actual connection and less like a script.

12. They avoid technology in dating.

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If they’ve been out of the scene long enough, dating apps and online flirting might feel completely foreign. They could prefer the idea of meeting people naturally, but today, apps are a big part of dating. Avoiding technology can limit their chances of meeting someone. Embracing some modern ways to connect can open doors they didn’t expect. It’s about finding a balance that feels comfortable.

13. They’re overly cautious.

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Being careful is one thing, but someone who’s been out of dating for a while might come across as overly guarded. They’re worried about getting hurt again or simply unsure of how to trust a new person. Their caution can create a wall that’s hard for the other person to get through. Opening up a bit, even slowly, can make a big difference. It’s about giving themselves a fair chance to connect again.

14. They seem surprised by dating culture.

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Dating culture changes fast, and someone who’s been out of it might feel like they’re entering a whole new world. Things like “ghosting,” “slow fades,” and “breadcrumbing” might seem bizarre, and they’re not sure how to respond. It can feel overwhelming at first, but catching up on the new norms can ease the adjustment. It’s all about learning the ropes one date at a time. Eventually, they’ll find their footing again in this new landscape.