Since I know PAR says he enjoys these tales of my past trials and tribulations:
5th & 6th Worst (tie) -- 1982, my sister's friend (also my first ever date) -- JD -- she was almost stalkerish and appeared to be one of those girls who might show up on the 3rd date in a wedding gown. I dumped her at an inopportune time (just as she was about to visit my sis for the weekend). Went to a house party with another girl, but JD was also there, she drank herself sick (age 16, not much liquor enforcement in upstate NY) in the woods, apparently french kissing every interested guy at the party, reportedly saying, "See what you are missing" out loud, even though I was not within sight or hearing range of her. One poor tipsy freshman kid (who idolized me b/c I was the high school QB and captain of the baseball team) came up to me and almost was crying, "I didn't know, man, I didn't know she was your girlfriend. I mean, she is just such an easy slut." It's OK, kid, I dumped her, go find her.....
1989 -- girl in my apartment complex -- CC -- went to a formal dance with her, her dancing made Elaine Benes look like Stacy Keibler. Having nothing better to do, we left to go make out at her place -- she was not overweight, but her body fat percentage had to be 25% plus. Like grabbing a garbage bag full of water. "Uh, well, I got a busy day tomorrow, better head on home...." Never dated again.
4th Worst -- 1985, fellow intern known as "Elvira" or "Joan Jett" -- real name EB -- after we had been interns together and she hadn't spoken to me once in 5 months, she came up to me in a bar and chastised me for not recognizing her subtle hints or asking her out. She was a heavy smoker, we "dated" once -- before things could properly proceed she drank 10 gin and tonics and ended up puking her guts out through the streets of Albany. I had to carry her home, place her in bed; her roommate came home and took over the death watch as I cleaned the vomit off the tile floor. She never spoke with me for the remaining 2 weeks of the internship and then left and went home.
3rd worst -- 1989, woman who lived at my apartment complex -- name was Lisa something -- "My boyfriend and I just broke up. You want to go out?" Sure. "Want to see a movie?" Sure. Get to the theater. "Oooh, 'Driving Miss Daisy'! Can we go, please?" Yuck, but OK, bonus points, HM, bonus points.... After the movie, "You know, it is all about sex with him. I do love him though. Well, thanks for the movie." Kisses, none, hugs, also none, holding hands -- nope. (Yes, I paid.)
2nd worst -- 1985, fellow intern, JC -- let's just say she was WAAAAAAAAAAAAAAAAAAAAY more worldly than the 21 year old country bumpkin HM. We only ventured out in public together three times -- twice she announced quite loudly (once in a mall, once in a dance bar) that she really didn't want me standing close to her or hanging around her on the dates because she needed more space and my lack of independence "really is a problem for me." I became so confused during the mall visit that I really didn't know what to do. I didn't have a cell phone, and we took one car, so I really couldn't figure out how I would ever see her if I just started walking around other stores by myself. The dance floor created very little confusion -- she just started slow dancing with another guy intern and loudly complaining about me. Even I knew that this was a bad sign...but still a narrowly better dating experience than...............:
1st worst -- 1990, Jan. blind date set up -- Pam M. - I had the distinct feeling that the girl was calculating how little affection she could demonstrate and still get taken out on a date to someplace else expensive. When I called and asked her out on a second date she said, "well, where would we go?" These subtle hints turned out to be leading somewhere when when she broke up with me before Valentine's Day with the infamous, "It is just getting too close to that day and I really don't want to have to spend it with you." Well, uh, thanks for the honesty?? I guess??? What do The Police call that in their song? -- "a humiliating kick in the crotch"?
If I can recall any more, I will let PAR know.