How One Man Decided To Make Dating Fun Again

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I'm 37 and single. I'm happy. I really am. OK, maybe I could be happier. As they say, the grass is always greener. That must be why I feel something like envy when I’m surrounded by my “relationship” friends. It doesn't help that more and more activities are starting to be planned as couple-friendly, and that I’m always sharing a room with my best friend when we travel. I love the guy, but waking up to his mug on every vacation is wearing thin. Men in their late 30s should be sharing a bed with their romantic partner, not booking two doubles in a hotel room and arguing over who gets the last clean towel. How did I get here?I have been in a few relationships, and I think of myself as a pretty good catch. I am ready to give it a real shot. That means one thing for certain. I have to go on dates. And dating sucks. But, the more I think about it, the more I realize that dating hasn’t always sucked. Why is it that lately I’d rather stay home and watch Mad Men than take a girl to dinner? Isn’t this supposed to be fun?When you're young, going on dates for the first time is pretty awesome. You feel like you’re growing up and starting to understand what being a man means through a woman's eyes -- a woman who isn’t your mother. Whether your parents dropped you off and picked you up, or you took the bus to meet a girl at the movies, those first dates were pretty magical. Not only were you experiencing some firsts in your life, but the mere prospect that someone of the opposite sex wanted to spend time with you was enough to keep you up the night before. It was exhilarating and terrifying, but there was also an indescribable romanticism that we weren’t even aware of at the time. I remember that feeling -- dates without the weight of anything besides a connection at its purest. I still maintain that my best relationships were in my teens. No agendas, just connecting over the mutual discovery. But that doesn't last long.Heading into my 20s, things began to shift a little. Some of the guys were sticking out relationships through college. While some of us were still trying to figure out who we were or what we wanted to do with our lives, there were a select few already mapping it out. They had the life plan, and they had the woman who was ready to be part of it. Some of us would be lingering at the bar until 3:30 to try to latch onto the nearest target, and these other guys would be heading home early. Their situation looked comfortable, but it wasn’t tempting enough for me to rethink what I had going on.So I was out there “dating.” Only this was no longer dating as I had come to know it. It was socializing. This type of socializing would lead to sex. If you ended up at the same bars or parties the following weekend, you would probably sleep together again. A few of these weekends in a row, and you would begin to ask yourself if this was someone you wanted to see again. But real dates were rare. It became more about networking and making sure you were meeting the right people and keeping up with the trends. Don't get me wrong, I had fun. But the shift had begun. Connecting with women started to require a little more than just being interested and asking. You had to have something to say, and if you wanted to find a woman worth her salt, you had to have direction. Suddenly, everybody’s scorecard had new categories. Continue Reading

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