Dating from a Male Perspective – September 26, 2013

brother graduatingI’ve mentioned my brother here before on the blog as well as had him do some modeling for a post about

online dating profiles.  But today I’m picking his brain for thoughts on dating, from the male perspective.  First though, let’s back up a bit.  My brother is 8 years younger than me (though you’d never know now).  He didn’t really date in high school and in general was somewhat shy around girls.  However, in the last few years I’ve seen him really step out and start dating more.  As I’ve witnessed his process I’m continually impressed with his straightforward and honorable behavior.  In fact, as I’ve gone on my own dates, I’ve often found myself wishing that my brother could teach seminars to men on dating.  Come on 30-year old dude, my brother is light years ahead of you.  So, I decided to pick his brain on his process in dating.

What was the turning point in your beginning to ask out women?

I realized that women are no different than men.  I mean, they’re different, but not a great mystery.  I started to treat them the same.  There’s a big myth that women are something crazy and you have to put up a big front and have big muscles.  But actually, they’ll respect you if you be yourself.

You just started asking women out.  Talk about that.

I figured screw it – what have I got to lose.  I stopped caring.  What’s the worst that can happen?

How did you learn how to ask out women?

I had two approaches.  With the first I would talk to a woman for a few minutes and then ask her out.  In the second approach I’d just walk up and ask for her number.  (Side note: my brother has absolutely done this before.  He ended up dating a girl he’d met that way at House of Blues.  She was shy so we nicknamed her “Shy Ronnie”).  I have the blunt and the tender approach.  I think they worked, because I didn’t learn how to do it.  I just did it.

I’ve noticed that you’re really great at communicating in dating.  What do you see the role of communication as in dating?

I don’t like there to be any gray area and it to be unclear whether or not it is a date.  I always say specifically “would you like to go out on a date”.  I go to coffee with friends, that doesn’t mean I’m dating them.  I make it know from step one that I want to ask you out.

What has contributed to your valuing that level of communication?  (Side note: my questions weren’t great for this interview, but I’m really proud of this one.  It actually sounds like I know what I’m talk about.)

Communication is what’ important.  Alex (Andrew’s lovely girlfriend) and I communicate about everything.  When we have an issue we make it known.  I dated a lot of girls before Alex and there just wasn’t that level of communication.

What should women hold out for in dating relationships?

Go on dates with other guys, but if you see any issues, bring it up.  A red flag today is a red flag tomorrow.  Especially if it’s against your core values.  Break it off.

Also, be treated with respect.  And he should pay for stuff!  I hate when guys don’t pay for stuff.  You should pay for at least 90% of stuff.  If he’s not paying for stuff upfront, then you should dump him.


Thanks Andrew for letting me pick your brain.  You’re awesome!

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