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

May 7, 2012  |  
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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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  • SetYourStandard

    18 yrs of age my standard set high. just told a guy about himself using some of these points! #NoScrubs

  • Tsk

    All of this is mainly common sense and I, as well as many other commentors, found these things out in our early twenties. But the one about being in your thirties and hating your job is ridiculous, someone could have a dream job that is scarce or doesn’t support a family so they could work another one to pay the bills especially in this economy not everyone can can affordd to do what they want unfortunately.

  • Guest

    No PDA”

    This is really bad advice. My husband comes from a culture where PDA is not really done. When we first met, he was extremely comfortable with it. Even though I’m affectionate, I compromised and let him be comfortable. Over the years, he has relaxed a little bit and now shows more PDA. 

  • L-Boogie

    Stay single.

  • Sw1242

    OMG… This whole article total hit home and i’m 26. just found out via fb my ex is engaged and was leading a double life with me… so please,please take heed to the signs!!! that little voice and signs will never lead you astray! you live and you learn!

  • Jerseryvixen

    Hmm the real real real talk is
    Entrepreneur =broke and lazy and looking for a way to not GET A JOB. They give the REAL entrepreneurs who planned properly and have a legitimate business a bad name!
    Drinks too much = alcoholics, many “catches” out here are functional alcoholics, you dont want that on your back ladies…

  • RenJennM

    By 22, I’ve learned most of this. Doesn’t take 4 or 5 times and a whole decade to get it.

    • mochaaa

      same here. 

  • At a quarter of a century (25) I’ve learned these things and more, and I’m healthy and happy while single because I’m not settling for these things or anything less. I would like to add:

    #7- The textaholic: If you’re getting sporadic, inconsistent, bland messages that take him/her hours to send, drop them like a hot potato. (Especially if you let them know you’re not big on texting.) People can be texting you while carrying on a whole other life with someone else. And, honestly, if someone’s feeling you, shouldn’t s/he rather talk on the phone or spend time in person with you?

    • Kisses

      Im so tired of men who think dating thru text is acceptable! I even had one guy argue with me–THROUGH TEXT–why I should be HAPPY that he chose to text me constantly, because it shows hes trying to get to know me for what’s on the inside…this is after I expressed to him that I wasn’t going out with him until he picked up the phone and called! He made it so difficult when all he had to do is CALL! I stopped responding because I figured either he was hiding something or just ridiculously stubborn! He can defend the virtues of text with the next one!

      • I completely agree! It’s like an epidemic. Good for you! The last guy I was with come talking about “is calling the only option?” Uh. No. Apparently my only option is to tell you to kick rocks. Dating through text is suspect and often disrespectful.

  • This is a great article. I know women who usually cringe at the idea of a man who says he’s starting his own business, like, “I hope you are working on your own business while you are at your REAL job.”

  • Mls2698

    Women can’t wait until their thirties to become smart. And entrepreneur always means not having a steady job because the average business takes three to five years to do well. Wait until your forties……..it will all change again.