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dating in your mid twenties

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Our twenties are a time for being free, for exploring, and for learning lessons through mistakes. In fact, it’s the best time to mess up because people will usually forgive you due to your age. That being said, some mistakes can follow us around forever. They have financial implications. They have health implications. They have legal implications. I worry about these TV shows that glorify the sloppy twenties in which the main characters are just laughing about the truly dangerous positions they put themselves in. In the real world, nobody gets to just walk off the set and take off their actor hat and return to their real lives after being reckless. If you know and love anyone in her twenties, warn her that these mistakes could follow her around for life.


Mild stalking

We all push the limits a little bit when we first have our hearts broken. We linger outside the guy’s work, hoping to “just run into him.” We discover what gym his new girlfriend goes to and join it, befriending her to learn why he chose her. And then…we can get a restraining order against us because, whoops, it’s not cute. And that’s on your record. If a guy dumps you, don’t obsess. Drop it.


Filing a restraining order

If you really feel your safety is at risk, that’s one thing. But a lot of twenty-somethings will file restraining orders just to be dramatic, against someone who didn’t deserve it. Bare in mind that’s on public record, and anyone who looks into it may feel you just love drama.


The blog posts

We all have that troubled artist phase when we think we know everything about love because we had 1.5 relationships and want to share our wisdom/vent to the Internet. And then we forget to delete those blog posts and future employers or boyfriends find them and think we’re unhinged.


Not using protection

Herpes never leaves and you have to disclose to every partner that you have it. Some are cool about it. Many aren’t. Chlamydia can damage your fertility health. HIV can kill you. Use protection.


Not using protection, part two

Getting pregnant, when you aren’t ready, isn’t always funny, romantic, cute, or quirky the way movies make it look. It can f*# up your career. Having an abortion will have serious emotional implications and could harm your fertility. Giving a child up for adoption may haunt you forever. Use protection.


Damaging his belongings

In a rage of passion, you may want to smash an ex’s windshield or even slander him. So, just keep in mind that he can sue you. You can get arrested. That’s on your record. That will affect your employment prospects.


Getting engaged too quickly and often

No matter how in love you feel with every man you date for 14 months, don’t get engaged until two years in (possibly three). You’ll be astounded at how many guys you break up with that you almost got engaged to. And having four broken engagements in your dating history makes you look a bit unstable.


Dating a lot in your industry

Dating in your industry is going to happen. But as a woman, if you’re in a male-dominated industry and date every man who takes an interest in you, you’ll get a reputation. Be SO discerning.


Dating the wrong way in your industry

As I said, dating within your industry is going to happen. But when you’re young, you can have this devil-may-care attitude where you don’t care what anyone thinks or says about your dating life. But it is important to have tact when dating within your industry, and you can read here on how to do that.


Financial entanglements

Something about being young really makes a person want to prove she is wise and ready to make “adult” decisions, which is why so many young couples will buy a car, house, or business together with a person they’ve only been with for a few years. And that’s a big financial mess when they inevitably break up. Do not get financially entangled with a man who is not your husband or serious, long-term domestic partner.


Sleeping with a friend’s man

It should seem obvious that someone shouldn’t do this, but we can be stupid in our twenties. Whoever the dude is, he isn’t worth it. He isn’t the one. He’s just not. Your friend, however, could be a lifelong friend if you don’t screw her over.



If you cheat when you’re young and dumb, it will follow you around. Even though you get older and wiser, future partners will be disturbed by the fact that you once cheated, and may believe you’re capable of doing it again.


Getting a romantic tattoo

Just don’t get a tattoo that has anything to do with a romantic relationship. Don’t do it. Maybe you can do it on your 35th wedding anniversary with a man, but not before that. That’s your body that you’re branding with the initials of someone you may hate one day.

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