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You Should Ask Him Out, If You Want To.

This is my new and studied position. Upon landing in Los Angeles and finding myself single at 30... Well, I read all The Books. You know, all those dating books? I know you know The Books, even if you haven't had the joy of reading them and trying to figure out the right and wrongs of the dating scene.

Even I, champion of the go-with-your-gut philosophy, bought into thinking that maybe, just maybe, The Books knew something I didn't know. So I did the best I could for years, reading and thinking and seeing what happened.

But at the same time, I find it very difficult to follow "rules" when they feel counter-intuitive. For example, if calling a guy is going to relieve some stress for me, or I just want to call the guy, I do. I don't play phone games and no book was going to change that. 'Cause I just don't have the patience.

I did, however, buy into the "men need to pursue" philosophy for a while. For one thing, it can be pretty freeing, because you just go about your business, working on being friendly and doing things you enjoy, and if someone's interested they ask you out. That's pretty cool, and I definitely recommend it as a general rule.

You know what though? A few months before The Boyfriend did exactly that - met me at a games night and asked me out - I met someone I found interesting, got his number from a mutual friend, and called and left a message asking him out for coffee. He never called back.

And sure, maybe he thought I was "desperate." Or maybe he just wasn't interested. Honestly, who the heck cares? I was interested, so I called and asked. There's just nothing wrong with that. There was just as much of a chance that he would bite, and we might have gone to enjoy some coffee and more get to know you.

Asking a guy out doesn't mean you're desperate. It doesn't mean you're too aggressive. It doesn't mean no one would ever ask you. It doesn't mean anything beyond, hey, you seem interesting, wanna get a coffee? (Or dinner, or go hiking, or whatever.) I felt great about it, to tell you the truth. It would have been nice if he was interested, but he wasn't and we both moved on.

So here's my philosophy, forever and for always, on whether you should ask him out if you want to: YES, YES, YES. If he thinks it means you're desperate - or my personal fav, thinks it means you're totally insanely into him - then who wants him anyway? The cool guys, if they're into you and smart enough to realize that a date is just a date, not a lifelong commitment nor a definitive statement of everlasting love, they just say yes.

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