Unable to start a relationship

Is it ever regretful to be humble, vulnerable and self-aware? 🤔 If so, I can't think of the scenario.

"Why do you want a relationship?"
To be supportive and supported while being a benefit to a shared community. There's something about the idea of having a positive, exponential effect on a ministry that I find fetching.

"What do you hope to get out of taking on a partner or spouse"
I don't go into a relationship with a transaction or exchange in mind. At this point in my life, I want to grow old, in mutual good health and sheer happiness, with the love of my life. If, within a certain period of time, I can't envision being able to do that with a partner then the relationship must end. In an amicable way, of course.

As for you, Chris, if you don't ask ladies out often, you'll often see few results 😉

Assuming you're not a cad about it, a lady will understand if you are "courting." I would assume it helps more if you have parameters/preferences for the kind of women you want to pursue. And then if you then want to get serious and date only one person with intent, then let it be known to the others.

Let it be known, also, that I'm not a cisgender male ( in case it's not obvious from the pp - self-isolation has been rough) so hopefully some fellas will come in here to help sort you out.

Two great responses above.

Re: ... a part of me believes that many eligible women have come to understand that starting a relationship isn't worth it, and if they are able to support themselves and be connected with Kids/grandkids/family/friends... staying single is a better option (not to generalize about all women, I wonder if the trend is in that direction)

I'm a woman & don't pretend to know what many women want... nor should anyone, imho... but most I've met don't want to be single... perhaps the ones you've met say so as they're not considering you as a partner for themselves for any host of reasons... basically, letting you down easily by saying they're fulfilled with their families & have no time to date. If you've already decided that many think a relationship isn't worth it... a very bold, defeating statement... it seems to me you're approaching dating/women with a half-hearted attitude & many will p/u on that, so it might be chasing them away.

What I've seen & experienced is most I've known met partners while out & about doing something they enjoyed. Rather than hanging out at a pub or trying to meet anonymous people on an online dating site or in a forum, who may represent themselves verbally & visually with varying degrees of honestly, I decided long ago that it's better for me to go out to do fun things. If I enjoy myself, the day was a success... if I happen to meet someone & there's a mutual interest, that's the bonus. And, if it doesn't happen often or at all, then I'm still doing something I enjoy.

I've personally known no one who's had long term success with meeting others online. Basically, I'm not looking for a pen pal to email or text or a friend-by-phone. And, I don't know if I'm attracted to someone based on a pic & a paragraph. I need a face-to-face encounter to see if there's interest. I also wouldn't want to meet friends online for the same reason... there might be much in common on paper, but in-person convos aren't interesting.

Depending on your degree of physical fitness, you can join walking/hiking/running/biking/skating/line dancing/yoga groups... many are split via age range. You already know the kinds of groups that are available... I've seen groups getting together to learn the Welsh language & have dinner once/mo... to brunchers who go to museums/plays/ballets together... to those who attend car shows & pot luck dinners.

You can also begin one of your own... a twice/wk, 2-mi walking group, open to all from 50-60, for example. Yahoo Groups is one place you can begin a group. Craigslist is another, but that can be a dicey site. Perhaps others can give further suggestions. You could also put up a Facebook page called Dayton 50+ Walkers Club or Orlando Golfing Brunchers to market to your specific group.

In my experience, dating isn't easy at any age... but, that's my opinion. However, with our current lockdown status, you've got plenty of time before you'll be asking a woman to lunch in a public place.

Best of luck.

BTW, you might consider joining the forums at city-data.com. It was originally set up as a relocation board, but it's grown exponentially & there are many forums that are general, as well as those for your city/state... many just want to chat about varying issues from grief, retirement, coupon clipping or recipes... some are age based... few but some occasionally meet up... normally in smaller areas & there've even been 1/2-dozen marriages over the past 15-yrs. In any event, check it out... you may find your niche there.

I'm about the same age as you, but married. So WTF do I know? I can only say that I like to be social and aspire to continue to make friends now that my kids have grown up.

The hard part of being this age is that, not only are many people married, but most people have chosen their friends as well. Younger people are great, but they don't share all the same interests and concerns as those in the same age group. Making friends at our age is just plain hard. For some reason, it's even harder for men than women. I've read a number of articles about it.

But, hard things can be accomplished with consistent effort. My approach has been to be part of a wide range of group activities, including run clubs, cycling clubs, book clubs, hiking clubs. Volunteer activities are going to be very important during the recovery to the current situation and I'm already thinking of how I can get involved.

I've certainly noticed that people respond positively when you offer your time to some activity and ask nothing in return. Who can resist that?

Take the red pill, my friend.

I just keep an open account at FarmersOnly .com