“I will say that I never have been the “flirty” type. That other post brought up that thought, wondering if something I’m *not* doing might be an issue.”

No, Robert, it’s not anything you’re *not* doing. That’s not the issue. I can tell you your issues. I’ve been telling you your issues. And I’ve also told you that you need to work with a therapist to overcome those issues. Nothing we, this community, or a date will tell you can change the outcome you seek.

Here are but a few:
1. You’re stuck in a 1950s fantasy. Example: You want a beautiful, late 20-soemthing or early 30-something woman with long hair to bear your children so you can have picture perfect holiday outings. Life is messy. This is not life.

2. You’re too stringent. Example A: Everything thing we’ve been telling you and you refuse to acknowledge, instead telling us why we’re wrong and you’re right. Example B: You refuse to update your way of communication to this century. Women don’t want someone who doesn’t appropriately use technology. Example C: You explained your dating semantics to @Copa explaining why, again, you’re right. First meet / first date… basically the same thing. Geesh.

3. You think the women you date owe you. They don’t owe you an explanation. of why they don’t want to go on a second date. Full Stop.

4. You haven’t had a relationship in years and you no longer have friends. It’s likely because you’re too set in your ways to actually be a good friend or partner. See item #2. HUGE RED FLAG.

You are doing something to turn people off. It’s something deep within you. You need a therapist to work through it.

In a nutshell, your problem is “Robert’s rules for how everything should be,” and that’s even why you ended your last relationship: You thought she should be a certain way – more ambitious. You don’t adapt to people or things or new information, you just keep going back to what you think. A lot of it is way outdated or just plain wrong, but you’re clinging to it, why? A therapist can help you figure that out.

You’re seriously spending money on a weight loss coach right now, but not therapy!?!?

You’re wasting all the time you might have left meeting a person you could connect with focusing on superficial shit that is not going to address the deep, deep issues you have making and keeping relationships with other people.

And yeah, your weight loss coach telling you that you are intense-to me, means you are probably scary, Robert! She’s trying to keep you as a client and was being honest but that’s eye opening feedback. Intense…I think we all know is an understatement. Stop asking her for her opinion on why women won’t date you. I don’t think you realize how inappropriate even that is. Stop asking women what’s wrong with you and see a therapist.

And I agree, you totally act like you’re not interested if you’d prefer to take the public bus home than get a ride home from a pleasant date. Jeez! I’m surprised she offered you that ride in the first place, but you whiffed it.

Robert, I know this can all feel like we’re “piling on”, but you have some of the longest threads on the site. People are here trying to help.

It feels a little like conversations are something you feel you need to “win.” Part of this comes from the combativeness here, and also due to clues like your weight loss coach saying you’re “intense.” Conversations with someone who always needs to win the conversation are tiring. If you’re doing this on dates, it will definitely be a turnoff.

Conversations are a collaboration, not a competition. Maybe the lessons of improv will be helpful here. Improv works off the concept of “yes and” when interacting with the other artists. I feel like you may be doing a lot of “no, actually …” when dealing with your dates. (The one who offered you a ride, but you “no, actually I’ll take the bus back” being a piece of evidence.)

“Yes and” means you don’t come in and completely negate what the person before you did. You take it and build upon it instead, but don’t just “no” it. That causes things to just stop. This doesn’t mean you just agree to everything anyone says, but you need to keep the flow going. If you just throw a “no” out there, it’s like hitting a wall. The flow of conversation just drops flat and there is effort to pick it up again. This effort is work. And nobody wants their dates (leisure activity) to be work.

“One woman did tell me that I was a gentleman and a pleasant person to talk to, but she felt that I showed no interest in her on the first meet.”

The “show no interest” part sounds a lot like whatever she talked about just got ignored rather than “yes and”-ed where you actually listen and follow up. It sounds like you may have taken the conversation and driven it where you wanted as soon as she stopped talking, rather than keeping it with her and showing that she interests you. (But, of course, going too far ends up in the “interrogation” land, which is also no fun. It really is a delicate dance.)

Also, please don’t compare your experience with that of a recent 29 year old woman writing in. Your experiences are nothing alike. You have had a problem connecting with men and women for years, decades, right? She’s had ten first dates that went nowhere.

“For example, a couple years ago I once went to an art museum exhibit on a first date – one I had been wanting to go see for weeks. I knew within 30 seconds of meeting him in person that we probably weren’t going to go out again.

I like those little examples. If I may ask, as I am genuinely curious, what did you see immediately upon seeing him that did not come out during the phone conversation? It seems so dramatic and sudden to me, the way you described it, that there *has* to be some indication beforehand.”

(I don’t know how to do the little insert quote thingie here, so I apologize if that doesn’t format correctly. Also I’m glad you like the examples; happy to give you some because I’ve had a ton, lol.)

So in that circumstance, we hadn’t talked on the phone. We had sent long messages back and forth on a dating app for probably 2-3 weeks. And I guess I am talking about a “first meet” rather than a first date, but yes, it is semantics at this point. I go through more upfront in getting to know men than a lot of people (especially younger Millennials and Gen Z) do, but I don’t have to talk on the phone before I meet them. So yeah, I took a risk, but I figured why not – he can write well, he seems smart, how bad could it be? Yeah, no.

I can’t pinpoint it either; I just knew within 30seconds-a minute that we weren’t going to vibe. We just didn’t have that connection in person.

There’s so much of this that’s difficult to put into words, I’m finding.

With the hobbies/interests thing: for me (women in general?) it is all about if you like the person you’re doing things with. I agree with you, Robert, that I used to not go to things/do things because I was single, and now if there’s something I want to do and I can’t find anyone to go with me I would much rather go alone. I’ve done everything alone from concerts, movies, restaurants, even traveling/vacations. So I applaud you in not letting that hold you back!

My most recent boyfriend and I were so different in many of our interests, but just enough were the same that we could share time together – and then we could go off and do our own things.

I say all this to say…you have to have the personality connection first, the “I want to spend time with this person no matter what we’re doing” first, and unfortunately – for most/all of us – that is very hard to find!

If a weight loss coach makes you feel more confident about yourself, awesome! I do agree with others in saying a therapist would probably help even more with some of the issues you’re having, if it’s a question of how to allocate resources (money and time). But I get it.