In Which I Describe My Dating Failures

Every day, people from all walks of life come up to me and say "hey, does this bookmark work on all books?" Their second question is, invariably, "hey, you're a good-looking, nice guy with a great sense of humor. How come you're not married yet?" Now, mind you, the person asking this is never a young, attractive, funny and nice girl who's looking to get lost in my eyes, but you can tell they mean well by their prying, overly-personal questions.

So to save time from answering these incessant questions, I will henceforth refer people to this post wherein I reveal how the universe has chosen to mock my desire to be in a committed, loving, monogamous relationship.

Let's start with true things that have happened to me.

• At least 3 times in my life, I've had a great first date with someone and then within a week heard some variation of the following story. "I really had a great time the other day. However, there was a missed connection (someone I used to like but who wasn't available at the time) who recently popped up. I'd really like to see where this leads, so I'm sorry to say I can't see you again."
  
  
• After asking someone out, I received a Christmas card from them. In the handwritten note inside, she started with a very lovely greeting, then proceeded to tell me that she had just broken up with someone and was not interested in going out with me. Who sends a Dear John Christmas card?
  
  
• About 3 hours before a new year was to begin, I got a call from a young lady I had been pursuing. She was on her way home to Massachusetts and she wanted to tell me that she wasn't interested in going out with me. Really, you not only did this on New Years Eve, but waited until you were out of state?
  
  
• Coming back to a girl's apartment after the first date and finding a flower and a card on her stoop. Thinking that was a bad omen, I still allowed myself to fall for her. Cut to six weeks later when she tells me the flower was from a "missed connection" and that she was dumping me for him.
  
  
• Paraphrased actual phone conversation. "Hi, this is Dave. I was wondering if you'd like to go out sometime." "Oh, I'd love to. What did you have in mind?" "Do you have a favorite restaurant?" Pause. "Wait, is this Jeff's friend, Dave?" "Yes." "Oh, I thought it was my boyfriend Dave." Needless to say, I did not get a date.
  
  
• In my 30's being hit on by a woman in her 40's at a bakery in Maine, who hinted, very strongly, that she liked the Whoopie pie.
  
  
• In my 40's being propositioned by a Russian in her 40's who worked at a Michael's Crafts. She actually said, "we could go in the bathroom...just kidding." But, I could tell she was not kidding.
  
  
• After asking someone out in high school, getting a full-page letter from them explaining why they think I'm a great guy, but they are not looking to date anyone at the time because of blah, blah, blah going on in their life. Within a month, they were dating someone.
  
  
• Doing most of the talking on the second date. On the third date, wherein we just watched a movie, she dropped me because I didn't talk enough.
  
  
• I'm the only guy in history who has had 'friends-with-benefits' without benefits.
  
  
• After a 10 year stretch of no serious relationships, my sister asked me "are you gay, not that there's anything wrong with that."

Since turnabout is fair play, here are some dumb things I have done on dates.

• Sitting through one and a half DVDs before I got up the courage to kiss a date for the first time. Keep in mind, she was making it very obvious that she wanted a kiss by snuggling up close and holding my hand, yet it still took me forever to make the move. Being the suave guy that I am, I wound up playing it very smooth. I said "hey," she turned her head towards me and I kissed her. She never let me forget the "hey."
  
  
• Leaning in for a goodnight kiss, her turning her head and me ending up kissing her ear!
  
  
• Not realizing the difference between a "heavy flirter" and a "light flirter." A heavy flirter will make very sexually suggestive remarks but have no intention of seeing them through. They rev the engine but don't want to go for a drive. A light flirter is more subdued and coy, but much more open to taking a drive around the block. Never take a heavy flirter at their word, it'll just frustrate you.
  
  
• Dated a woman who was separated but not yet divorced. Always wait for the divorce to be final and ideally at least a year behind her. Trust me, you do not want the emotional baggage inherent with the end of a marriage.
  
  
• In college I was house sitting for my boss, who lived in a log cabin in the woods (true story.) One night I brought my girlfriend over for a dinner. A storm came up and knocked a power line across the only road out. We had to spend the night. Let's just say, I didn't take advantage of what could have been a very romantic evening.
  
  
• Wrote a note asking her to reconsider her decision to dump me.
  
  
• Dated women who had so much baggage, you needed a U-Haul to go to dinner.
  
  
• Not only did I look at another woman during a date, I made a comment about her outfit. In my defense, she was wearing overalls and nothing is sexier than a woman in overalls. But, still, it was an idiotic thing to do.
  

Thus endeth the lesson.