17 Older Women On The One Thing They Wish They Knew About Dating In Their 20s

Dating is one of those things I don’t know if any of us ever have it completely figured out but we can certainly learn from our past experiences and gain insight and knowledge on what to do differently in the future. I love talking to my mom about my love life because her wisdom is invaluable to me. She always reminds me of what’s important. I decided to ask her and several other beautiful older women in my life and across the internet on the one thing they wish they would have known about dating when they were in their 20s. Some of the answers are inspiring, others are heartbreaking. Hopefully, we can all take a few lessons on life and love from these women.


“A man does not nor ever will define you as a woman. Love yourself before you can truly love someone else. If a man does not respect you when you are dating he will never respect you as a wife. Do not sacrifice yourself, your needs, or dreams for any man. If he can’t embrace and celebrate those with you, then walk away. Always have and make time for girlfriends …I always did and am so grateful; I value my friendships so much. Above all else, enjoy your 20s. It’s a time to learn who you are. And don’t be so serious. Laugh, dance, and relationships will come. I wish someone would have told and engraved these in my 20s brain.” – Lisa


“I wish I would have taken the time to enjoy the present. Instead I was always worrying about the future and I didn’t enjoy the every day joys of every day life. I wish I would have let myself enjoy it more than I did.” – Diane


“I wish I had known that I didn’t need a man to make me feel good about myself …especially one who didn’t care about me or my feelings. I also wish I had had the sense to know that being with someone to validate my thoughts about my appearance and self worth was stupid. I guess the most important thing I wish was that I could have felt comfortable enough to talk to my mom. To me….having that person in your corner when you have fears and doubts about yourself is invaluable.” – Melanie


“1. Love a lot. It’s ok to fall in love over and over because you learn something new about yourself each time you go through what you think is a gut wrenching break up. 2. Everyone should have at least 1 one night stand and not feel guilty about it. 3. Be social. Always be available to go on road trips, vacations, dinner, coffee, parties or whatever you are asked to do, you won’t regret it. 4. When you’re in your 20s and you are dating, walk away quickly when you realize that the guy you are dating is not right for you. Don’t be afraid to let them go and try again.” – Nikki


“Never date somebody that you wouldn’t marry because you never know who you might fall in love with. Also, don’t stay with someone whose faults you can’t live with. We all have faults so choose someone who’s faults you can live with.” – Sue


“I wish I would have known that it was okay to break up with someone sooner than I did. I always tried to make things work, I always tried to self-sacrifice in relationships because I thought it made me stronger and because I thought in the end it would all work out. As soon as you feel that gut instinct that something isn’t right, LISTEN. That is your body using it’s own cues that you’re not in the right relationship. Always trust your gut instinct.” – Rose


“Don’t ditch your friends as soon as you get a boyfriend. Your friends will always remember that. They want you to be happy, of course, but don’t focus all of your attention on a boyfriend because if it ultimately ends up not working out your friends are going to be the ones to help you pick up the pieces. Stay true to your friendships. Stay balanced.” – Melissa


“If early on in a relationship you realize you’re the one putting in all of the effort to get your partner to see you, end it. Dating, like all relationships, is a two way street. If someone is having a busy time at work or school and they aren’t available, that’s fine, but they need to communicate that. If they’re never around and you’re the one begging them to spend time with you, don’t bother. A man should consider himself lucky to even have a lady’s time. You’ll realize that there are plenty of wonderful men out there who will give you the attention you deserve.” – Anne


“Don’t lose sight on your own dreams and hopes for the future just because you fall in love. I think it’s easy to succumb to relationships and to feel content in just being someone’s girlfriend or spouse. Then 20 years later you realize you should have acted on the things you wanted to do but didn’t because you got preoccupied in love.” – Sheryl


“Don’t put too much pressure on finding the perfect one in your 20s. Your 20s are about falling in love with yourself. Take risks, try new things, dare to dream. Become confident in yourself and your abilities as a person. You have the rest of your life to date and be with another person.” – Tina


“I wish someone would have told me it’s okay to fail. It’s okay to make mistakes, to choose the wrong person, to date people who might not end your your partner for life but still let you learn from them. For a long time I used to beat myself up over failed romances but then as I got older I realized every person, every experience, is a chance to grow and evolve as a person. I kissed men who were terrible for me, dated people far longer than I should have but in the end it made me stronger. When I finally figured out what I liked and didn’t like about a man I was ready to find that person and settle down.” – Meg


“I wish that I would have felt more open in talking with my mom and my friends about what was going on in the early stages of my first serious relationship. It was borderline abusive and I felt ashamed and stupid for letting a man do what he did to me. I guess I felt like they wouldn’t have understood or they would have laughed or not believed me. I wish I wouldn’t have bottled it up for as long as I did. And I guess I wish I wouldn’t have been foolish enough to believe that a drinking man can change.” – Sophie


“I don’t think I have any regrets about dating in my 20s but I guess I wish I didn’t feel like I had to settle for the first person to fall in love with me. I was so young and I just felt lucky that someone else could look at me and see me as something special. I guess you could say my self-esteem was low back then. We had a 30 year marriage and I did love him but sometimes I wonder what would have happened if I would have met someone else. I think when you’re that young you should be more free.” – Meredith


“Don’t worry too much about what people think. That’s what I wish more than anything. I was in an interracial relationship when I was 21 and we kept it secret for a long time but soon our families found out and we were shamed into breaking up. I couldn’t handle the guilt of betraying my father so I let my one true love go. I still think of him and wonder what could have been 25 years later.” – Sonya


“I wish I would have enjoyed the present more in my life and relationships in 20s. I was always looking towards the future and thinking about what ‘could be’ instead of being appreciate of what was. I think I lost a lot of time like that. I should have enjoyed those young moments more.” – Fatima


“I wish I would have said yes to more things – both in dating and daily life. I was so scared of taking chances and risks. My friends would want to go off on a roadtrip and I’d be scared about the thought of a few girls being alone on the road. So they’d go and I’d be home working at the diner next to campus for a week. Then they’d come back with a tan and fun stories. And with dating there was once a nice Irish boy who wanted to take me out more than anything but I said no because he was Protestant and I’m Catholic and I didn’t think my family would ever approve. I guess I wish I would have just been more open-minded in life because now, as I get older, all I can think about are the chances I never took.” – Kathy


“Figure out your bottom line in dating and relationships. Don’t pretend to be someone you’re not or as if you’re okay with certain behaviors if it really upsets you. Be strong. Fill up your own heart. Give yourself love and gratitude every single day. I wish I would have kept this in mind in my 20s.” – SherryThought Catalog Logo Mark


Former senior staff writer and producer at Thought Catalog.

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