21 Dating Tips I wish I could Have Shared With My 21 year-old Self

dating tips

By Jackie Pilossoph, Founder, Divorced Girl Smiling, the place to find trusted, vetted divorce professionals, a podcast, website and mobile app.

When I was 21, I had my whole life ahead of me. I felt unafraid of almost anything. Physically, I felt wonderful. I was free-spirited and happy most of the time. All that said, at 21, I was so naive, I made so many mistakes, and I didn’t have wisdom, self-confidence and common sense when it came to dating.  Now in my 50’s, I have the opposite of what I had and didn’t have at 21 (except I’m still happy. ) It would have been so nice to be able to give myself dating tips!

Ever wish you could travel back to the past,  walk up to yourself and give yourself some really, really good, smart dating tips?

If that was possible, think about how many less mistakes you’d have made, how much better some of your life decisions would have been, and for the purposes of this article, how much happier you’d have been in your romantic relationships.

Here are 21 dating tips I wish I could have shared with my 21 year-old self:

1. Don’t make a decision on whether or not you like him in the first two minutes of the date.

Talk to him with an open mind. I was once on a blind date and did not find him attractive at all, at the beginning. Halfway into dinner, I fell in love, and ended up dating him for 6 months, until he broke up with me!


5 Tips to Choosing the Best Divorce Lawyer For You


2. Every relationship is bliss for at least the first year.

I call it “the courtesy phase.” After the courtesy phase is when two people get to know each other’s true personality.

3. Arguing is normal in every relationship.

Instead of getting upset and crying, learn how to communicate with each other more effectively.

4. You either trust him or you don’t.

There’s no in between, so stop trying to rationalize it and talk yourself into the fact that you trust him. If you have any doubts, then you don’t trust him. Period.


Want Financial Security After Divorce?


5. It’s never too late to break it off, even if the invitations have already gone out.

Sometimes people don’t know how to get out of relationships. I have been in this situation. You feel like you are too deep into it, you don’t want to hurt the person, and your family loves him. So, you just stay, even though you know it’s wrong. I get it. But, although it might be painful and uncomfortable, you need to end it if it’s not right. You don’t want to end up going through another divorce!

6. Trust your friends and family’s opinion.

Great dating tip: They know you and have your best interest at heart. If they don’t like him, there’s probably a valid reason.

7. Don’t be afraid to be alone.

It’s better to be alone than to be with the wrong person. If you learn how  how to be happy alone,  it takes all the pressure off feeling like you need to meet someone. Falling in love should be a want, not a need.

8. Don’t pressure someone to get more serious.

Relationships need a lot of time to breathe, especially relationships after divorce. If the relationship isn’t going at the pace you want, you have two options: Let him get there himself, i.e. wait it out, or break up. To force it by putting pressure on someone never, ever works.


How Does Mediation Work? Mediators Offer a Step-by-Step Process


9. There’s a fine line when it comes to why you might not want to get married to the person you are in a relationship with.

Be honest with yourself. Is it normal fear or is he not the one? Don’t let people say, “You’re just scared because of the divorce.” Even if that’s the case, you shouldn’t get married until you are jumping up and down for joy thinking about it.

10. When you marry him, you are marrying his family.

You might be spending an exorbitant amount of time with them. Know that going in. Also, as time goes by, your partner will want to spend more and more time with his or her family. That’s just the way it is, and there is nothing wrong with that.

11. Never stop being kind and respectful to your spouse. Ever.

Kindness and being respectful are the things that lead to loyalty and to physical attraction, believe it or not. No one wants to have sex with someone they don’t feel respects them or who is mean to them. On the other hand, when someone feels truly loved and adored, that’s when sex is the best.

12. Cheating isn’t a problem either of you have, it’s a problem in your relationship.

13. He will never change.

Whatever bugs you now will only continue to bug you worse in the future. Live with it or break up. You can change little things, like asking the person to be neater, or take out the garbage, and you can tell someone in a nice way what bothers you. That’s normal. But, you are never going to change the core of the person.

A cheater doesn’t change, a person who isn’t ambitious is never going to be ambitious, a person who smokes pot all the time isn’t going to stop, and a drinker won’t stop drinking. A gambler won’t stop gambling. And someone who hasn’t worked on his or her past, won’t suddenly get emotionally healthy. It’s sad, but it’s reality.

14. If you don’t like yourself, your relationship will suffer.

Your spouse will annoy you because you are actually annoying yourself. You might blame your unhappiness on your spouse when in reality, you just aren’t happy with yourself.

15. When you become a Mrs. and have kids, don’t lose your professional identity.

I did it and I paid for it–financially and emotionally. I’m not saying that being a stay-at-home mom isn’t a good idea, but make sure you think long and hard about what you want as a mom. Don’t feel guilty if going back to work is your decision. Your kids will see a wonderful role model, and you will appreciate them more.

16. Enjoy each other.

Couples might forget sometimes, that the whole point of being in a relationship is to have fun and enjoy your lives together. So, it’s important to never stop dating your partner, and to plan fun things to do together.

17. Sex only gets boring with someone if you let it.

Sex is work. It’s fun work, though. You have to keep things sexy and work at it. Why? Because having sex helps couples connect and bond. Foreplay is so important, and foreplay is going on all the time–from kind gestures to treating each other with respect, to thoughtfulness, to saying something nice.

18. Saying I love you is nice, but saying I’m sorry is better.

19. Never stop going out with your girlfriends, and encourage him to go out with his friends.

This way, no one feels co-dependent.

20. Love him (or her). A lot.

All men and women need to feel loved and appreciated, especially after divorce.

21. Trust you gut. It will never be wrong.

Why are these 21 dating tips useful? Because you don’t have to be 21 to implement them. It’s never too late to change the way you look at love, to get into a happy healthy relationship, and to be truly fulfilled in your love life.

I met the love of my life 6 years ago when I was 49. He is getting the best of me, because of what I learned in past relationships and in life. Had I met him at 21, I highly doubt it would have worked. I might have looked better, but inside, I look a lot better now! So you do!

Like this article? Check out, “9 Signs of a Healthy Romantic Relationship”



Listen to the Divorced Girl Smiling podcast View the DGS trusted divorce professionals! Divorced Girl Smiling is now offering a private, no-cost, one-on-one phone consult

Sign up for the Divorced Girl Smiling newsletter to get articles on divorce and dating.

Sign up


    Divorced Girl Smiling welcome video
    Jackie Pilossoph

    Editor-in-chief: Jackie Pilossoph

    Jackie Pilossoph is the Founder of Divorced Girl Smiling, the media company that connects people facing with divorce to trusted, vetted divorce professionals. Pilossoph is a former NBC affiliate television journalist and Chicago Tribune/Pioneer Press features reporter. Her syndicated column, Love Essentially was published in the Chicago Tribune/Pioneer Press and Tribune owned publications for 7 1/2 years. Pilossoph holds a Masters degree in journalism from Boston University. Learn more at: DivorcedGirlSmiling.com

    Leave a Reply

    Your email address will not be published. Required fields are marked *