I am a 27 years old straight male. I have an apartment in the city, a good but eventful job, I coach little league in my free time, still find time do to things with friends and family and be active. I have a great life and I am thankful for it.
Dating on the other hand for me is a disaster. Meeting women is fine and seems to be the easy part, but getting second and third dates down is very difficult and they seem grow disinterested. Socially my life is nowhere near as fast and hard as it was when I was younger, I am fairly conservative in terms of my partying and social habits now, and if I go out for drinks or to a party I am usually home at a decent hour and except for a few occasions, I keep myself in good condition.
I can’t determine if the women I meet aren’t ready to grow up, are intimidated by me and don’t want to compete with my schedule, or if I am a legitimately boring person and have a terrible approach to dating. Maybe a combination of all three.
I’d love to hear what you think.
Is It Me?
Dear Is It Me,
The fact that you can easily get a first date tells me only one thing: your problem is not your looks. Which means… your problem is in either your personality on the first date or your taste in women.
Let’s start with your personality. Some people can be relaxed and show their date exactly who they are right out of the gate. They have nothing to hide and put zero pressure on the evening so the person sitting across from them at dinner/drinks gets a really good idea about who that person actually is. That sort of calm confidence is really attractive and charming.
Then there are those that do not make the best first impression. It doesn’t mean these people are less than those that do, it just means this person is a little harder to figure out and often times can come across as a smug asshole without meaning to. Maybe you’re one of these people? If so, that’s an easy fix: ask her tons of questions about her and her life. People love to talk about themselves and she’ll probably walk away from that first date thinking you were a really good listener.
It’s also a sneaky great test. If she just lets you continue to ask her questions and never asks you, “Well what about you?” then you know she’s a selfish brat who only cares about herself.
Which brings me to my next point… are you picking the wrong women? You sound pretty mature for 27 – are you dating younger women who still want to stay out at bars till 2 am? If so, then yes, to them you are boring. They want to party and not be home “at a decent hour” to wake up and coach little league baseball. Those types of women are years away from wanting the lifestyle you seem to have.
Try dating women (older?) who have their shit together. See if they can appreciate a calmer, more mature man and are willing to ask, “Well what about you.”
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