Online dating advice requested

Miscellaneous and Personal Stuff I Must Share
21

I am a guy and been on line dating not very successfuly for about two years. I believe in being honest, and waiting to a second date is maybe over the line? Dunno.

My profile clearly says separated but not yet officially divorced. And I understand that is a deal breaker for 90% of the women out there, but I personally would rather be upfront. When I first started dating, on the first date I would have to explain about my kids (including a special needs child that needed a whole family to care for her), and that was the reason I wasn’t yet divorced.

I’ve kinda progressed to trading a few messages. And if I think this could be a good fit, I lay out a few things that “might be a deal breaker for you.” I think that is better than meeting once or twice, and then letting the deal breakers slip. YMMV

I like to meet very early on for coffee or lunch or something pretty casual just to understand what the in person vibe is and if there’s a spark. I don’t know how many times I met someone who’s photos were 10 years and 10 kilograms out of date. That was always a deal breaker because it demonstrated a complete lack of honesty to me. For chrissakes, I’m bald and I know that’s a deal breaker for a % of women. I don’t try to hide it with a hat on my profile, a toupee or a combover, and then hope I’m so amazing in person that it overcomes the shock,

Net net, I’d try to intrigue the other person into a least a few messages first, and then either in a message or on the first meet, just honestly lay out the situation.

22

That’s the stereotype, and IF THAT’S THE SITUATION, it’s a red flag for many people. Anyone would be wary of a man-boy who’s living with Mom because he’ll never grow up and be independent.

My advice? After some low-commitment coffee/lunches, and on the first or second dinner/movie/concert evening, explain that Mom’s living with you but it’s temporary. She had a cancer scare but she’s better now, you’re planning on getting a place after the housing market calms down, whatever*. That should allay most people’s fears**…

*First, make sure it’s the truth. Are you positive you’re not staying with Mom forever because it’s easier than facing the world?

**and they are FEARS. I think everyone’s just waiting for “that great guy” to have some hidden character trait that’ll keep him from being an acceptable partner. Is it a gambling addiction? Is he a Swiftie? Or is he tied to Mother’s apron strings?

23

When (not if) the truth is found out, it will not go well. The first thing the will go through their mind is “What other big lies were told?”