Hip to the Game: Red Flags We Overlook In Our 20’s And Look Out For In Our 30’s

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When you’re young, you let a lot of things slide when getting to know a guy. You see behaviors as “incidental.” You don’t pick up on patterns. You don’t realize that A leads to B. But, as you date more men, you start to realize that the following behaviors all correlate with one thing: possible bad boyfriend material.

New entrepreneur

In your early twenties, when a guy tells you he’s starting his own business you see ambition, passion, money (let’s be real here), intelligence, curiosity about the world and so much more. Later in life, when a man tells you he’s starting over and thinking about starting a new business, you see a guy who is too busy to see you and even in the few hours a week he can, his brain is on the loan he just took out to start that business. A new entrepreneur sells his heart to his business until it is established and might not be the best person to try and pursue a relationship with right now.


With guys in their early twenties, you expect them to not be totally comfortable being lovey-dovey yet. They’re still trying to prove they’re a “man.” But, later, if a man you’re dating refuses to hold your hand in public, you know it’s not really a good thing. He might have trouble being affectionate and caring in general or he cares too much about what other people think. Essentially, all things that would make a relationship with him difficult.


Fresh out of a relationship

We overlook this detail when we meet a guy in our early twenties because, well, college relationships aren’t all that serious anyways. Also, we like playing the savior to a guy with a broken heart. But as you get older, if someone tells you they’re fresh out of a year+ relationship, you realize they are still very much tied to that other person. And even if they were willing to date you, you’d be cleaning up the mess another woman made.

Last minute plans

It’s fun when you’re young—a guy calls and sounds so enthusiastic about seeing you. He says, “Be ready in an hour” and you are because you see this as “he wanted to see me so badly, he threw caution to the wind and didn’t care if he was being rude.” When you’re older you realize that guys who really care about you and want something serious make sure ahead of time that they get penciled into your schedule.

He hates his job

Who doesn’t fresh out of college? At that time, you bond over complaining about mean bosses and long hours. But, later in life, if a man is still hating his job you wonder—is he too lazy to find another? How, this late in life, has he not found his passion? Is he just not a passionate person?

Infrequent calls

You accept too many excuses when you are young and when a man calls after two weeks of not contacting you with a simple, “Hey I’ve been busy with work,” you’ve forgiven him and are ready to go on another date. Later you learn that, everybody has life happening to them, and they make time for the people they care about. You essentially realize if a guy is only calling you up 2 or 3 times a month, you’re a plaything to him. And that frequency of interaction is never going to increase.


Drinks too much

When you’re young, all you care about when a guy drinks a lot is that he says cute things, gets handsy and overall pays you more attention than when he is sober because his inhibitions go down. When you get older, if a man consistently gets too drunk on dates, you see this as he does not respect you or care about you enough to stay sober so that he can actually remember the conversations you have and get to know you.

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