We all do things we think better of later on.
We're human that way.
Cut yourself some slack.

We all make decisions that we later regret, but in all honesty we’d probably do the same thing over. I submit that your decision was a good one. You seem to be berating yourself for not having the courage to be open and honest, but is that rational?

You are demonstrating all kinds of courage by telling us all this. All of us are just humans, not perfect angels. You are perfectly okay as you are. You have the right amount of courage.

It might be true that you missed an opportunity, but what of it? There’s a down side to every perceived opportunity and we have to weigh both options. AND perhaps you helped that person by your presence. Romance is not a requirement.

I am just now getting rid of guilt in regard to my deceptive manner with women when I was a stupid young man hoping to get laid. Oddly they seem to understand and forgive—they have their own deceptiveness.

Let it all go and enjoy the miracle of each passing moment.

I hope you have forgiven yourself for that.

Regret is a terrible thing... you need to forgive yourself, learn and move on. Time travel is not possible so there is nothing you can do about a decision you made (based on very realistic scenarios) years ago.

Your assessment of your issues and your regrets are genuine. But I think you've given yourself too harsh a sentence.

We are all different Robert, so it's hard to judge someone else's decision on a situation such as yours back then. I can certainly relate. After I had already been dating my late wife for a couple years, she and I learned that her mother had dementia and my wife had already known or maybe suspected that her grandmother has also had it, so I was in a position around the time we got married of either deciding to cut my losses and split with her, or instead, choose to live with hope rather than fear, that she might not inherit the family genetics of dementia like the women before her or at least not develop it until age 75, like her mother. If I remember right, my wife was in her mid-50s at that time. I chose the latter and she didn't begin to develop dementia until almost age 69, in 2011. So we had 16 good years of dating and marriage before it went bad with the dementia.

Regrets, sure I have a few, but they are more about how I handled her dementia some of the time, esp. in the early stages as I was trying to accept it and figure out how to cope with it. But as far as, should I have stayed in the relationship or not after finding out what was probably going to happen with her? Not a bit, it was hell for much of the time during her dementia, but that relationship was still worth it, to me at least. I cannot speak for anyone else as to if it would be worth it. We can only make those choices for ourselves and not judge or choose for others because, in the end, we are the ones who have to do the suffering for those choices and live with the results, esp. not somebody else sitting in judgement who hasn't been thru it. Thanks for sharing some very honest, genuine stuff. You are an ok guy, Robert.

Regrets, you have a few?
You are lucky, my friend.
I have a lot! But, please, forgive me for not sharing them publicly, 99% of them are just too personal/private for that.

I've let more than a few good things go in my years on this rock. I've also taken a few leaps of faith that we're ill-advised and found myself in some very sticky situations as a result. You never can tell which is gonna be which. You can make a big mistake either way. Dwelling in that self-judgement is always counterproductive and never accomplishes anything. Let that shit go. Easier to say than to do, I realize. Becoming involved with helping others can help you get outside of your own head, but we all do it in our own way. All my best to you, brother, hang in there and good luck.

In life, nothing ventured, nothing gained.

Ohferpetessake, a hundred miles is about an hour + a half, less than an hour if you both go halfway.
That said, did you try changing your criteria a teensy bit here & there to determine what the major sticking point was? I myself would want to know!

I'm sorry. It's hard to live with a big regret like that. We can only move forward.

Even a few short years of joy is better than none at all. Everything is a risk.

I see your regret and I do understand it. What I am also seeing is the situation as you thought it was. The question is "was this the true situation?" Your regret should center on the fact that you will never know.

I can't say much more than welcome to the human race and it's good of you to care.

On the far extreme, my point is enjoy life while you got it.

BTW, I view dating sites as the pits. It's unlikely a person will get love of their life. However like the lottery, sometimes people win. Don't bet the rent. The likely result is you'll develop an on line friend you'll never see. Good chance you might wind up talking to them on the phone as well as too good a chance they live too far away to date. Beats watching TV on lonesome nights.

Then there's my ex-biz partner, may the parole board be turning him down now. He was computer illiterate but he'd have dozens of women for his annual cross country motorcycle run. He got their addresses out of magazines with ads for women who wanted to write prison inmates. He'd stop at the places they lived over a wildly zigzaging course from Pensacola, Florida to Sturgis, South Dakota. He had no real plans to date any of them. All he wanted is a series of one night stands.

Once a year he went to a motorcycle rally in Sturgis, leaving a trail of freaked out women behind him. He'd rape and assault (or was that assault first, rape second -- I forget) them before leaving for the next woman, next town. It's why I hope the patrol board keeps turning him down.

I had to mention Gary's trail of one night stands after you'd mentioned once a year you visited Match.com. Once a year, Gary went to Sturgis driving drunk and chugging beer all the way for ~14,000 miles round trip. The guy was a psychotic alcoholic with poor personal hygiene. There ought be a screen play written about his annual trip.

He was a good subject for a college level creative writing paper. I got an A+. He was an unforgettable guy I ought to forget.

What, you couldn't find anyone among the fake profiles Match posts as entertainment?

Match sucks. Don't waste your time.

As for love and connection, keep trying, but don't waste too much time; finding a mate is a sucker's bet in a such a screwed up culture.

The old Beatles song "There are Places" comes to mind.

Consider, like you said, that at the time you may not have been ready for that type of relationship. Maybe this sounds cliché, but we do the best we can with what we know, and when we know better, we do better... Lots of things I passed up on because I wasn't ready, and I've lived in regret for many of them. I can't do that anymore, regret doesn't help me live now or move forward. The only thing I can do with the past is learn from it, but I can't live there... Don't give up on something just because you felt you missed your opportunity. You never know what you'll encounter.

Theres a big difference between "connecting" and "the one" (If that's just a ideological concept, is a debate for another day). Match appeals to people looking for "the one", right or wrong, and you may have done her a huge favor by not letting your desire for a "connection" stop her from looking for "the one". But yeah, you might be wrong.

Thanks for sharing this. I don't have any words of wisdom but I would encourage you to get out there and try again, it's never too late.

You may want to consider the possibility that if everyone seems to be out of step with you, then perhaps you could be the one who is out of step? Maybe there are things about yourself you could consider changing to become more compatible with other humans on this planet? Just a thought.

I'm amazed that back in the day Match had a long questionnaire. Nowadays, I think about the only one that still does is E-Harmony. I would rather use a site that had that than one that didn't, but I have a couple issues with E-Harmony that keep me from using them. One is that the site is for people who want marriage and I have no intention of doing that again, simply because it isn't necessary or something I want at my age without kids. Secondly, they have a dysthymia scale as part of their personality survey and I would undoubtedly get rejected by them as a member because of that, so I'm not going to bother with them.