Was there one that you wanted to ask but just couldn’t find the nerve?
And not to leave the ladies out, was there a guy you knew darn well wanted to ask you out but he blew it because he didn’t ask?

I’m not sure there were any that I didn’t approach as I was always pretty confident. However, Sandy was the girl that caught my eye in first grade and it took me until Senior year to ask her out. I knew what the answer was going to be but I wasn't going to carry around “I should have asked” the rest of my life. So I drove to her house one Saturday and asked her out. She did turn me down but she did it with so much class that I walked back to my car thinking wow, brains and class? Now I want her even more.
So, did you ask or not?

I did. Took her out to a movie, enjoyed a terrific evening, then went off to the rigs for a summer job. She had graduated, went on to become a very successful lawyer. I went back to high school. Never talked to her again. In my heart of hearts I know had I bothered to stay in touch there may have been more...No loss, only happy thoughts. My life has been beyond my dreams. Choice makes life, right?

Lucy.

Still love her.

Carol.

Blond. Athletic. Cross country and track. Cheerleader. Intelligent. Voice like Lauren Bacall.

Wealthy father. Uber wealthy stepfather.

As the Dierks Bentley song says “what was I thinking?”

There were a few "coulda, shoulda. woulda" but the main one was Sadie. I went to college in the evenings while working full time. I started at a community college because it was low cost and I could cover the baseline courses. Sadie was in one of my classes. We would talk over coffee during the break. Very pretty, wicked smart, great smile. I lacked the confidence to ask her out. We met by chance 5 years later, we were both in relationships. I hope she found everything she wished for in life.
Me? I'm flying in my tax... no that's not it, I met a lovely woman at a canoe club meeting, we have been married for 42 years, life is good.

Cute neighbor girl that I had a crush on. Got the nerve to ask her out. So I went to her house to get to know her a bit better. During the discussion, I find out that she was a used up promiscuous party girl. No thanks, I couldn't leave fast enough.

Years later, I find out she was rushing to have a family. Married young, and had a lot of kids.

While there were a few, Cathy was "the one". We came to be in the same class in 4th grade and I had an immediate crush on her. Her dad got transferred and they moved away during 8th and 9th grades. They came back for 10th grade and I'll never forget seeing her for the first time in 2 years, leaning up against the tree outside of the band room. The crush was back even harder. Such a sweet girl; attractive and not stuck up. The quintessential girl next door. However, I was very shy and just couldn't bring myself to ask her out. We graduated, went to different colleges and moved on with our lives. For our 20th class reunion, we were both invited to a small, pre-reunion get-together hosted by a mutual friend. We had a great time catching up. As everyone was saying goodbye, we shared a hug that could have been deemed inappropriate as we were both married. We held each other tightly and for quite a long time. No words were spoken but the moment was intense. I think there were regrets for both of us in that moment but we simply said goodbye and returned to our lives. Now, 25 years later, I have no idea where she is or how she is doing but I do still fondly think of her every once in a while.

Jacky. High school. She was beautiful and every guy knew it. She gave me a neck and shoulder massage on the bus one night returning from our jazz band competition. Was dark. She was sitting behind me. She reached forward and massaged my neck. I responded and she continued for the next long while. We talked quietly after. I never asked her out because I couldn’t believe a girl like her would be interested in a dork like me.

Nope. Never shy and I considered girls like vacuum cleaner sales. Knock on 100 doors, 10 will let you in, 1 will buy.

I married the last one. We were together 30 years. None since.

April 13, 1974. Met a beautiful, smart, young lady, clearly way out of my league. Fully expecting to be shot down, I clumsily asked her out.

This coming May will be our 47th wedding anniversary.

Morgan Fairchild.

Natalie Marshall

It wasn't that I didn't have the nerve. She either was dating someone when I was single, or I was dating someone when she was single. We became friends but never crossed that line. She was Swedish, and could have been the spokesmodel for the Swedish Bikini Team. Super smart, too.

At our 10 yr class reunion she confessed to me that she had the same frustrations I did about it.

Who knows if dating would have worked out. We both went our own directions after college. But I am of the philosophy of never look back with regrets. I wouldn't be where I am now if I'd made different decisions, good and bad.

Jane Sullivan, met her at the first Earth Day, 4/22/1970, we picked up trash in the streets of Richmond. I thought we connected. She moved with her family to Doylestown before the summer was over, never saw her again. I still think of her fondly. Probably a grandmother by now!

There were many others, I was fairly shy in my teens and early 20's, with no athletic prowess, and less self-confidence. I tried hard to make up for my slow start in my late 20's and 30's, didn't seem to do me any harm.

My fourth wife...

quote:

Originally posted by Krazeehorse:
Morgan Fairchild.

The Patsy Ann McClenny 'Morgan Fairchild'??

My older sister's friend (neighbor). She is 2 years older. I really like her. I visited her few times in her school and had lunch few times. She knows I like her. But she was not interested. I ended up with someone else. Years later, she wrote me a letter saying she was sorry she didn't took me seriously and wished it was her I ended up with. That letter was 35 years ago.

Deb.

We went to different schools so I didn't meet her until high school though I'd had a "she's cute!" crush on her for a couple of years by then. My friend met her at the same time and asked her out right away while I wanted to talk to her. He got the date and I got friend-zoned before Friend Zone was officially a thing.

However, we got to be really good friends over the next couple of years but she was always dating someone else when I'd call to ask her out and I'd always hear about her new boyfriend. I finally gave up but when we were in college, I went to see my girlfriend. She and Deb lived on the same floor and were friends. My GF broke up with me a short time later and suggested that I ask Deb out. "You'd be perfect together," she said, except for the fact that we were hours apart which led to our breakup.

I didn't see Deb again for 20-something years until we were both happily married to someone else. We had a good talk and she asked why I'd never asked her out when we were young. I told the truth and we had a good laugh about it and are still friends today.

My entire life, I’ve never asked any girls out. Only one asked me out, and she would become the future Mrs Q.

Vanessa Marcil. She’s an actress. If you look up pics of her you’ll recognize.

I was standing in line for concessions at Laguna Seca one year for MotoGP. She had these white, tight, pants on, and she was extremely fit. She was in line with her friends, turned back to me and gave me a huge smile. Ear to ear. The ladies were conversing about me. I knew who she was. But she’s a damn actress on TV and I was too intimidated. I don’t like in Cali. But I should have just asked. I would have signed a NDA. She was definitely single at the time.