25 Relationship Lessons I've Learned In 25 Years

I'm about to turn 25, which would mean that I'm now eligible to rent a car — except that I live in New York City and don't have a license, rendering my birthday merely symbolic. However, reaching my quarter-life mark does mean I've learned a quarter of the important relationship lessons I'll learn throughout my life (unless my rate of learning speeds up or slows down. Not sure exactly how this stuff works.)

Like most 25-year-olds in the U.S. today, I am unmarried and plan to remain that way for a while, but I have had my share of relationships, dates, hookups, breakups, and everything in between (well, not everything), and I definitely have a different approach to dating from when I first started. The last 25 years (or, more accurately, the latter portion of them) have brought me a number of great dating experiences as well as unpleasant ones, and I'm trying to learn from both — but given the disproportionate number of "don't"s on this list, it looks like I've learned most from the bad ones. I suppose our mistakes truly are teachable moments.

Here are 25 "do"s and "don't"s my 25 years of living (but not of dating, because that would be oddly precocious) have taught me.


1. DO Seek Out Someone Who Asks The Big Questions

When I can spend a date talking about the meaning of happiness, ethics, and healthy relationships, I view it as an excellent sign because these are the kinds of issues people have to discuss to make a relationship work.

2. DO Go Ahead And Send That Follow-Up Text

As this charming song by The Blow (and this oddly popular fan video) describes, sitting by your phone and waiting for a text can be a form of torture. Put yourself out of your misery by getting in touch with last night's date yourself. As long as you're not sending multiple unreciprocated messages in a row, you won't come off too forward; you'll come off polite and interested.

3. DO Establish Your Own Happiness Before Seeking Out A Relationship

Unhappy people don't have much to give because they're expending all their energy just trying to get by. If you're unhappy, other people will sense that you aren't able to offer much to a relationship at the moment. Get yourself to a good place — whether that means getting a new job, moving, or seeking treatment for physical or mental health issues — before you try to share your life with someone else.

4. DO Play The Field

When you meet someone you're really into, it's tempting to get into "OMG THEY'RE SO GREAT" mode and forget about everyone else out there. But until you've made your relationship exclusive, you both have the right to date other people. No matter how perfect someone seems for you, there could be someone else even more perfect for you. This mentality is destructive once you're in a relationship, but while you're still casually dating, exploring other prospects will only make you more confident when you decide to settle down with one.

5. DO Honor Your Feelings, Even The Petty Ones

For a while, I struggled with the fact that I felt jealous about the prospect of a love interest also being interested in someone else. Polyamory just made so much sense — but I couldn't do it. I'm finally OK with that. Sure, jealousy is petty, but I shouldn't put myself in situations that make me miserable just to avoid being petty.

6. DO Remember You Don't Know Everything About Someone At First

It's so easy to get your heart set on someone in the very beginning, when they've put their best foot forward and shown you all the things that would make them a great partner. These qualities are usually genuine, but there are also often other qualities that people don't demonstrate right away. More people have "issues" than you'd expect. The fact that someone has a thousand amazing qualities doesn't mean they don't have some bad ones too, so wait it out and see if you can handle them at their worst as well as their best before committing to a relationship with both versions.

7. DO Have Fun!

Screening potential life partners can be exhausting. Sometimes you really just need to make out with someone on a dance floor or engage in a sexting session with someone you would never even date. Also try to enjoy your dates themselves for what they are rather than worrying about what they'll lead to. Often, this attitude can actually improve your ability to connect with someone.

8. DO Let Go Of The "Rules" You Have Learned About Sex

I grew up believing that sex could only happen in the context of a committed relationship, or else... or else I'm not sure, actually. You'll go blind? You'll be damaged goods? Something like that. I am generally a serial monogamist, but some of the best sex I've had was with someone I wasn't even dating. The fact that we cared about and respected each other was more important than the label. I wondered at the time if I would regret it, but I actually just regret not starting sooner!

9. DO Be Picky

If you keep telling yourself that the person you're looking for isn't out there, you will never find them! Knowing what you want helps you hone in on people who merit your attention and filter out those who don't, which actually makes it easier to find the right match in the long run.

10. DO Be Playful

The ability to make each other laugh can get couples through a lot. Telling nonsensical jokes, making fools of yourselves dancing, and making ridiculous faces and noises can also be quite a bonding experience.


1. DON'T Ask Other People Why They Rejected You

Trust yourself to know when you've royally screwed up and when it's just not a match. If you've royally screwed up, you already know that, so their opinion is unnecessary. If it's just not a match, it's not your fault, so it doesn't really matter what the reason is.

2. DON'T Apologize For Who You Are

Someone on OkCupid once asked me what I do with my free time. I told him I don't have much lately, so I mostly just hang out with my friends and family — "I'm boring, I guess," I added. I shouldn't have sold myself short like that. I'm dedicated to my work and make time for the people I love during the little free time I have. I should've been proud of that. We create the lives we live for a reason, so nobody else should make us question our chosen lifestyles.

3. DON'T Get Back Together With An Ex

I'll admit there are a few exceptions to this one. I know couples that have broken up and gotten back together, and their second run lasted. But in general, getting back together with an ex erases the hard work you've done getting over them and usually heralds another breakup — especially if you've already been on and off.

4. DON'T Stick Around To Hope That Someone Will "Grow On You"

Beauty and the Beastis a lovely story, but in real life, lack of initial attraction usually predicts a permanent lack of attraction. If a friend organically grows on you, great, but don't try to force a relationship just because you like someone's personality and think they might grow on you. Usually, you'll only end up leading them on.

5. DON'T Rearrange Your Plans For A Date

Sometimes it feels like you must put everything aside to accept an invitation from a special someone. But if someone really wants to see you, they'll wait for your work and social schedules to clear up. Having a life is attractive.

6. DON'T Spend More Than Half An Hour Getting Ready For A Date

Someone else's attraction to you is mostly out of your control — but it's hard to give up the little control you have and therefore tempting to spend as much time improving your appearance as your schedule will allow. The struggle is real. But, trust me, primping or lack thereof will not make or break anyone's attraction to you. Nobody has ever said to me, "Now that your makeup's off, I'm no longer feeling it." Especially after half an hour, you start to see diminishing returns on your efforts anyway.

7. DON'T Feel Like You Need A Reason To Turn Someone Down

I've stuck around in a few relationships a bit too long because I couldn't put my finger on what was off. The people I was unenthusiastically dating seemed nice, smart, and good-looking, so why would I not want to date them? In all these cases, I can now look back and pinpoint what was wrong. I should have trusted myself at the time and considered my lack of enthusiasm a good enough reason to break things off.

8. DON'T Feel Like You Owe Anyone A "Chance"

"But he's such a nice guy." Women hear this phrase with nauseating frequency. "You should give him a chance." Here's the thing, though: 1. Being nice isn't a free pass to a date with a person of your choice, and 2. Your allotment of chances is nobody else's business.

9. DON'T Online-Stalk Someone You're Dating

This can get really discouraging — especially if you stalk them on the dating app where you met and find out they've been on there, probably talking to other people, in the past hour. Same goes for searching their Facebook photos for other people they could possibly be dating. It's tough for a lot of us to deal with the fact that as we're starting to fall for someone, they could be falling for someone else. But try to keep your confidence up and focus on your own relationship. You can cross that bridge if you ever get there.

10. DON'T Hook Up With Someone You're Not Comfortable Around

If you're going to get physical with someone to any extent, you should feel relaxed, appreciated, and safe. If you feel nervous, insecure, or unwanted, you will be out of the moment and enjoy yourself less. These feelings are also a sign that someone isn't treating you quite right.

11. DON'T Let Anyone Gaslight You

I've put up with way too many of what I've come to call reverse fights, where a partner gets mad at me for being mad at them. This is a form of gaslighting — making someone doubt their own perceptions. It can sound like "you're over-reacting," "you're being too sensitive," or "you're being too hard on me." It's never wrong to say how something made you feel. If someone upsets you, they should care and want to help, not make you feel even worse in order to deflect responsibility.

12. DON'T Hinge Your Self-Esteem On Another Person

It definitely gives you an ego boost when someone finds you irresistible. But what if they change their mind? People change their minds all the time, so in order to be resilient, your self-esteem must be independent of everyone else. Relatedly...

13. DON'T Turn To A Significant Other For Validation

If you're struggling with low self-esteem, particularly poor body image, your partner may seem like a natural recourse. And sometimes, they can say the perfect thing to make you feel better about yourself. But if they say the wrong thing, it can mess with your self-image even further and cause unnecessary resentment. The validation we gain from others is usually temporary, anyway, so it's better to learn how to comfort yourself in these situations.

14. DON'T Take People's Behavior On Dating Site's Seriously

Those sites are full of trolls. I once got a message on OkCupid reading "You look like a child molester." That doesn't make any freaking sense! People say all sorts of crazy things to everyone. Those who don't message you or engage in a conversation and then drop the ball also aren't to be taken seriously. I constantly get matched with people on dating apps who don't message me even though they swiped "yes." Online dating brings out everyone's lazy side.

15. DON'T Settle

It may seem like amusing yourself with a friend with benefits for the time being won't detract from finding the committed relationship you really want, or that a relationship destined for failure is better than no relationship at all. But when we settle for a B or C until we find an A, we just push our encounter with that A further into the future. When we settle, it's usually because somewhere deep down, we believe that what we truly want is unattainable. But the only way to discover whether it is attainable is to commit to finding it — and to believe you deserve it.

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