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11 Dating Lessons I Wish I'd Learned In My Twenties

Corinne Dobbas
Updated on September 15, 2020
Corinne Dobbas
Dietitian+Wellness Coach
Last updated on September 15, 2020

You know that girl who has a timeline for when she'll get married, knows how many kids she's going to have, and even has their names picked out? Well, that was me. And everything was going according to plan—until I got dumped.

That heartbreak cut raw and deep. But ultimately, it allowed me to find strength, happiness, and peace that only I could give myself. It also put me back in the dating arena. But this time, thanks to a hefty load of personal work, it was different. My last relationship (once I moved past the pain) was full of beautiful learning opportunities.

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Here are 11 dating insights I wish I'd learned a long time ago:

1. You should be having fun.

Dating is supposed to be fun! You're meeting new people, having new experiences, doing new things. If you go into a date with that expectation, your outcome will dramatically change. Create fun experiences—go hiking, play miniature golf, hit up a theme park, try bowling, head to the zoo, sign up for a cooking class, etc.

The more fun the actual date experience is, the more fun you and your date will have. And guess what? People bond over interactive new experiences. And even if you don't, at least it was fun. Get creative.

2. Expectations make it hard to have fun.

When we have expectations, we're not living in the moment. And when we're not living in the moment, it's hard to really enjoy another's company. For example, if you're on Date 8, and you're wondering about when/if you're going to become exclusive, then it's pretty hard to actually enjoy your experiences together, which is necessary if you ever want to get to that exclusive space (if it's meant to be).

This very grounded, centered approach to living is attractive. You're not freaking out about the future; you're living in the moment and you're confident. When you're here you know that if it's meant to work out, it will.

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3. Your truth always matters.

Have a question? Feel like something is off? Are you ready to take it to the next level and see if your date is too? Speak your truth. You literally have nothing to lose—except being with someone who isn't on the same page or jeopardizing your own feelings, which always (eventually) turns out badly.

In any relationship, especially a dating relationship, you should be with someone who respects you for kindly and compassionately speaking your truth. Point blank.

4. How much you like them matters as much as how much they like you.

It can be too easy to lose yourself in the beginning dating phases and let, "Do they like me?!" become the dominant thought, especially when you really like the other person.

Remind yourself that you're just getting to know the person and this takes time. You need to decide if they're truly the right fit for you. And once you relax, be yourself, and give the process time, you'll find out.

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5. Boundaries are sexy.

Are you not okay with less than 24 hours' notice to go on a date? Is sex before exclusive commitment a big no for you? Is friend and/or solo time (removed from your partner) key for your personal growth?

What are your boundaries? Think about it and stick to them (sometimes they get foggy when your vision is blurred by new love). And remember, you're still just getting to know the other person.

You need to take care of you so you can show up a healthier, happier person when dating. Plus, boundaries foster respect. They indicate you know yourself well enough to know what you need and that you think you're worth it. And that's sexy.

6. You're going to date a lot.

Finding "your person" can take some time—and a good number of dates. Know that there's nothing wrong with you. It's a process. Have fun. Get to know someone new, and their story.

Ultimately, dating is a process that'll help you not only learn more about others but also about yourself. What you like. What you don't. And eventually, when you meet your match, your past experiences will help you be a better partner.

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7. You can't take anything personally.

Whether they didn't ask you out again, didn't text back, or seemingly dropped off the face of the Earth, no big deal. Move on to the next. That person has officially done the work for you and weeded themselves out of your dating world. Send them love and compassion, thank them for the dating experience, and move on.

Remember, there are a gazillion reasons why something like that could've happened. Don't try to read their minds and don't take it personally. We all have our own stuff and they might be working through theirs. And if you really want to know what happened, ask from a place of compassion and honesty. You've got nothing to lose.

8. Without sex, everything is much less complicated.

Sex opens a whole new can of worms. And if you're already feeling weird about a dating situation, most likely, it won't be the answer to your problems. Not to mention, once you start sleeping with someone you're not exclusive with, it makes dating others so much more confusing.

Inevitably, even if just casual, you will become (in some way) more attached to the other person. Figure out where you stand here and know that the right person won't stop seeing you just because you're not sleeping with them, though the wrong ones might.

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9. You attract what you're putting out there.

We attract others who are on the same vibration. So if you're constantly meeting others who are "so not the right match," it may be time to look at what you're putting out into the universe. It may also be time for some inner work. If you find yourself here, that's beautiful. We can't change anything we're not aware of. And you're aware.

10. Be open to meeting someone wherever.

Get out there and join dating sites, ask your friends and/or close colleagues to set you up, smile at people in grocery stores, go to functions you're invited to. And most importantly, invest time in your passion. Love hiking? Join a hiking club. Are you a yoga fiend? Ask your yogi friends if they have friends, go on a retreat, take a training. Adore dancing? Sign up for a dancing class.

And whether you meet the love of your life or not, you'll be doing things you love and having new experiences, which will make you a healthier, happier human. And healthy, happy humans with wide-open hearts are downright attractive. And guess what? They get asked out more. Get out there.

11. The "right one" will always be there.

Above all else, know that your "person" will always be there, no matter what. Whatever silly thing you say, whatever vulnerable thing you share, whatever boundary you put up, if it's the right person, there's nothing you can say or do that will prevent that relationship from unfolding. So have faith. Have fun. And be you.

Corinne Dobbas author page.
Corinne Dobbas
Dietitian+Wellness Coach

Corinne Dobbas is a mindful eating dietitian & life coach who helps women ditch the diet, date without drama & learn how to like themselves. Download her free Enough-ness Manifesto to remind you you're awesome on even your worst days at