The issue is not when the last date was, but how non-datable you've become. If you get very set in your ways, that will make you harder to date.
I hear a lot that driving too far is not worth it. I'm not up for dating someone 100 miles away either. Gas costs too much for that shit. But seriously, are you willing to date someone 30minutes away or only 10 minutes. I suggest as long as the drive is about the same or less than your drive to work, consider it. Unless you live in LA of NYC. A twenty travel can easily become over an hour with traffic, construction, weather or the fargin' Q going local.
Another bad habit is not wanting to go to new places. I am guilty of this. But after living in LA I've been to Vietnamese, French, Japanese and Thai. This may not sound like a big deal, but if you're the person who hates Thai food you won't be invited.
Most places have one dish that is newbie friendly. Even if the food that hits the plate is not your favorite eat a little. Pick at it a bit and be polite. We all know the "I wasn't very hungry," line means, it tasted like dirty socks. I said that once about misu soup. "Tastes like feet." That little comment flew like a rock. I'm not sure if this is true, but I have heard that spending years eating dinner over the sink can create really bad table manners. Mouth closed, please.
Beyond food, don't be afraid of certain movies or activities. I'm not big on board games, bowling, watching football or any sports for that matter but go with it. I've always had a really good time doing things I wouldn't normally do on my own. It's not the game, it's the people.
Prime example, not a big baseball fan, but the neighborhood had a Dodgers BBQ during the world series. I had a great time. Also ended listening to one of the games on the radio. It became a mini-series to me, like Tales of the City. I wanted to find out the ending. I tried to watch the world series on my own the next year, and well I found myself watching Law & Order, an episode from 2003. Again, it's not the game it's the people. Honestly, if the hot girl you like loves book clubs, would you be willing to read a few books? Don't go over-board, you still need to be yourself. Bowling, football, looking at comic books I've done but I wouldn't take up needle point or for me, I wouldn't go camping.
She'll may notice you are not as excited and if asked, admit it's not something you'd normally do, but you'd love to try it. Yes, say "you love to try it." Unless it's something there is no way in hell... Be prepared to suck at it, but just laugh. I haven't played pool since I could get into a bar legally. When a girl wanted to hit a pool hall I said, "dude I'm gonna suck." My first few shots were cool, but the second game was painful. I had to laugh as my stripes just kept rolling around the table.
Try not be real negative about yourself. I've been on dates where the woman went on and on about how she couldn't get dates because she was too old. Don't go over board about how you're heavy, smoke too much or watch too much TV. Then tell the person how any day now you're going to change.
Bad bad bad! Don't tell your date, that if only you had someone in your life you'd be motivated to change. That sounds needy and screams co-dependency. I'll only take care of myself for someone special, but not for myself.
I'm not going to go into you should do it for you.. blah blah. You already know that, and honestly your outlook does change when the life you lead is yours. Just know..People want to be invited into your life. They want to discover you, not have someone build a life around theirs.
Bend a little, Grasshopper. Be like the wind not the uhm something not bendable.
The wind does not break a tree that bends
~ Sukuma proverb (Africa)
The tree that does not bend with the wind will be broken by the wind
~ Mandarin Chinese proverb

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