Confessions of a Chronic Dater

Over a span of three months, I went on dates with forty-three different women. Yup, that’s right. Forty-three women. Of course, this would be considered “off-season” by the late Wilt Chamberlain, but it is a number that many men would envy. On a typical week, I would have a lunch date, a drink date, and a movie date.

Before you think that I am scum, I want to provide a disclaimer. I was dumped by a girlfriend of seven years. We began going out our junior year of high school. Even a week before she unceremoniously dumped me, I thought that “Rani” was the girl I was going to marry.

To help me get over Rani, my friends took it upon themselves to set me up with any eligible ladies that they could find. Of course, I wanted to feel better about myself, so I became pro-active in my dating search. But I was new to this whole dating scene as I had effectively been off the market during the prime of our dating lives.

Lesson #1: Let women set you up with a blind date.

I realized that my gal friends were better at setting me up than my buds. Usually, the gals were trying to set me up with blind dates who shared same interests and had great personalities. To be fair, I told them that I would not date anyone who was not pretty. My buddies usually tried to set me up with the hottest-looking gals. I certainly appreciated the gesture, and I even made out with a handful of them. However, I was so used to being in a relationship that the idea of sharing a beautiful conversation seemed more memorable than sharing bodily fluids.

Lesson #2: Women love to be approached.

During the three months of my dating spree, I learned one lesson. Women want to be approached by men. Sure, there are a handful of men-haters (lesbians), but even many lesbians want to feel that they are attractive to the male species. Maybe some of them were using the lesbian excuse to get away from me. I began trying to make conversation with good-looking women wherever I went. Supermarket, Starbucks, convenience store, bus stop. Perhaps I even hit on you. I needed to feel that women were receptive to my charms. And while I managed to snag a phone number from a dozen (out of perhaps sixty), I still enjoyed my conversation. I think a 20 percent success rate isn’t bad. Plus, I am sure that the other fifty (except the three lesbians) appreciated that I took a keen interest in them.

Lesson #3: Be open-minded.

Initially, I made assumptions about what I wanted in my blind date, so I was quick to pre-judge based on appearance. However, the really fun dates turned out to be when we both relaxed and had a good time. I did not have chemistry with all of them (in fact, most of them), but I still enjoyed the conversation.

Lesson #4: Treat them well.

During the seven years with Rani, I realized that I took things for granted. As I hit the dating scene again, I held the door for my date and tried to put my date’s enjoyment above mine. Also, I made it a point to call or email my dates a few days later to let them know that I had a good time. No, I didn’t say, “Let’s do this again sometimes.” Even if it didn’t work out, a phone call made the date feel special. I probably took Rani for granted during the latter stages of our relationship.

Lesson #5: Don’t burn bridges.

This is an extension of Lesson #4. Even if the date didn’t work out in terms of chemistry or mutual attraction or whatever, I made sure that my date had a wonderful evening. Five of my dates were actually referrals from my previous blind-dates. I even had a few second dates from the referrals. The women’s gossip network is better linked than the world wide web. So if you are one of the “good” guys, you will have no difficulties in finding the right one.


So what did I do after my three months of dating? During the seven years with Rani, I began getting too comfortable in my relationship. The three wonderful months made me realize that I am an attractive, witty, and charming guy. I needed that affirmation. I also met women who seemed to gel better with me than when Rani and I first started dating. Yes, I miss her, but I can also accept the fact that she wasn’t the one for me. As for the forty-three women, there are three that really clicked with me. I look forward to knowing them better and seeing if any long-term relationship can develop with one of them.

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