What if we hit it off, go on a date, and past relationships come up? If I admitted I’ve never really had one—or told a white lie about never being in a long-term relationship—would that be a dealbreaker?
Let’s go further. Say we’ve been dating for a while, things get intimate, and I admit I’ve never done this before. Would that scare you off?
I feel so hopeless sometimes. I’m trying to stay positive, putting myself out there, and being bolder than I’ve ever been. But when I think about how far behind I feel and the roadblocks ahead, it’s overwhelming. It seems impossible to catch up.
I’m also clueless about meeting someone. I’m trying to be more social at work and in my usual spots (though I’d never date a coworker). I’m not into bars or clubs, and even when I see someone attractive, I don’t know how—or if—I should approach them. I’ve ruled out online dating, and meetup.com in my area is all card games and walking groups for people 50+. Any tips would be a huge help.
Let’s take a deep breath together. The fact that you’re 40 and haven’t been in a relationship? It’s not a red flag—it’s just a detail. Life is messy and non-linear. Some people marry their high school sweetheart; others find their person at 50. You’re not broken or defective because your story looks different. What matters is how you show up now, not the past you can’t change.
Now, about telling someone you haven’t been in a relationship. Let me say this loud and clear: honesty always wins. If you try to bury this or tell a little white lie, it’s going to eat at you. Vulnerability is the bedrock of connection. If you’re dating someone who sees your lack of experience as a dealbreaker, they’re doing you a favor. They’re not your person. The right person will see the real you and value your courage and self-awareness.
Let’s talk about intimacy. If you admit, “Hey, I’ve never done this before,” and they bolt? Again, that’s their baggage, not yours. The right partner will meet you with kindness, curiosity, and patience. They’ll want to navigate those waters with you, not shame you for where you are. You’re not behind. You’re just on your journey, and that’s okay.
When it comes to meeting someone, you’ve already identified a crucial truth: you need to be yourself. Don’t force yourself into environments that don’t align with who you are. You’re not a bar or club guy? Fine. That’s not your space. Instead, lean into your interests and passions. Are there hobbies you’ve always wanted to explore? Local events or organizations that interest you? Even volunteering for a cause you care about can connect you with like-minded people. Authenticity is magnetic.
Another thing: learn to be okay with putting yourself out there imperfectly. Confidence doesn’t mean having all the answers—it means taking the risk anyway. See someone attractive? Approach them like you would a new friend. No cheesy pick-up lines or rehearsed scripts—just be curious and authentic. Something as simple as “Hi, I noticed you [insert context: reading this book, looking at this art, walking this trail] and wanted to say hello” can go a long way.
I know you’re overwhelmed by the idea of being “behind,” but let me challenge that narrative. Behind what? Life isn’t a race. Nobody is keeping score except you. Stop grading yourself on how you think you measure up to others, and focus on building the life and relationships you want—at your own pace.
You’re already doing hard things—being bolder, putting yourself out there, facing your insecurities. That’s incredible! It shows you’re growing, and growth is what matters. Keep showing up. Keep being kind to yourself. And remember: the person you’re looking for isn’t looking for perfection—they’re looking for someone real, and that’s exactly who you are.
You’ve got this. One step, one conversation, one day at a time.