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.
It is not a red flag. It is an unanswered question.
People are not scared off by lack of experience nearly as much as they are scared off by insecurity, secrecy, and dishonesty. If you lie about your past, that will hurt you way more than the truth ever will.
At 40, if you calmly say, “I have not really been in a relationship before, but I am working on building that part of my life now,” the right person will not run. The wrong person will. Good. Let them go.
Same with intimacy. The issue is not inexperience. The issue is whether you turn it into shame. If you act like it is something embarrassing or hide it until the last second, it creates distrust. If you are honest, grounded, and open to learning, it can actually build connection.
You are not behind. You just have not practiced yet. That is it.
But here is where I am going to push you a bit. You say you are putting yourself out there, but then you list all the ways you are not. No bars. No apps. No coworkers. No meetups. You freeze when you see someone.
That is not putting yourself out there. That is waiting for a low risk, perfect situation that does not exist.
You are going to have to get uncomfortable.
You do not need to walk up to strangers and deliver some smooth line. You need to practice being a normal human who can say one sentence.
“Hey, I see you here a lot. What do you usually get?”
That is it. No pressure. No performance.
And you need reps. Lots of them. Talking to people with zero expectation. Men, women, old, young. You are not behind in relationships. You are undertrained in basic social risk.
Also, you ruled out online dating. Why? That is one of the few places where people are actually there to meet someone. You are making this ten times harder than it needs to be.
Here is the truth you need to hear. This is not impossible. It is just unfamiliar and uncomfortable. But if you keep avoiding the exact situations that would teach you, you will stay stuck.
Start small. Be honest. Stop hiding. Get reps.
You do not need to catch up. You need to start.