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

By Jackie Pilossoph, Editor-in-chief, Divorced Girl Smiling, Love Essentially columnist and author

dating tips

In my “Love Essentially” column, published today in Sun-Times Media, I offer dating tips by way of wishing I could travel back to the year 1987 when I was 21 years old and give them to me! Enjoy the column!

21  Tips I Wish I could Have Shared With My 21 Year-Old Self

Ever wish you could travel back to the past, say when you were about 21 years old, walk up to yourself and give you some really, really good, smart advice?

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 column, how much happier you’d have been in your romantic relationships.

Here are 21 tips I wish I could have shared with my 21 year-old self about dating, relationships and marriage:

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.

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.

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

6. Trust your friends and family’s opinion. They know you and have your best interest at heart.

7. Don’t be afraid to be alone, and figure out how to be happy alone. Falling in love should be a want, not a need.

8. Don’t pressure your guy to get serious. Let him get there himself.

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?

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.

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

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.

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

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

16. Enjoy each other. That’s why you got married. Never stop dating.

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

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.

20. Love him. A lot. All men and women need to feel loved and appreciated.

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

Why is this information useful? Besides sharing these 21 tips with someone who actually is 21, realizing certain things we might have done differently helps us in our relationships today and moving forward. That might be a more delicate way of saying that life experience and wisdom are two of the few but valuable benefits of being over 40!






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Jackie Pilossoph

Editor-in-chief: Jackie Pilossoph

Divorce is a journey. Live it with grace, courage and gratitude. Peace and joy are on the way! Jackie Pilossoph is the creator and Editor-In-Chief of Divorced Girl Smiling. The author of the novels, Divorced Girl Smiling and Free Gift With Purchase, Pilossoph also writes the weekly dating and relationships advice column, “Love Essentially”, published in the Chicago Tribune Pioneer Press and the Chicago Tribune online. Additionally, she is a Huffington Post contributor. Pilossoph holds a Masters degree in journalism from Boston University.

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