If you could travel back in time, what pearls of wisdom would you pass on to your single self during each decade of your dating history? Here, men and women from all ages weigh in with advice they wish they’d known in their twenties, thirties, forties — and beyond!
What people in their 30s wish they’d known while dating in their 20s…
1) Try being friends with someone first
“I would tell my younger self that ‘fools rush in.’ [When I was] in my twenties, I didn’t take very much time to get to know a guy. If I was physically attracted to him and that attraction was mutual, a relationship would form quickly. This did not allow me enough time to identify [potential] character flaws — or even realize if I liked him past the initial butterfly stages. Needless to say, I found myself in and out of relationships during my late twenties. In my thirties I am much more relaxed, reserved and patient. I still haven’t found The One and I’m OK with that. I realize now that friendship is the foundation for a wonderful relationship that lasts!”
– Erica Binnum, 33, Long Beach, CA
2) Push through your fear of rejection
“The advice I’d give my younger self is that you miss 100 percent of the shots you don’t take. Ego is a man’s worst enemy, and it stops us from approaching the women we want — all because we’re afraid of rejection or worried we’re not good enough. Push the envelope and see what’s possible for yourself; go talk to anyone and everyone that strikes your fancy. If they’re not interested, it’s not a reflection on you, because they don’t even know you. Once you start getting some positive feedback — i.e., you get rejected less and less — then this process becomes a lot easier and actually turns into something that’s fun and enjoyable.”
– Jordan Harbinger, 32, Los Angeles, CA
3) Don’t let The One get away just because you’re young
“I am currently planning my wedding with someone I recently reconnected with after 10 years: the bartender who made me drinks on my 21st birthday. It took us both a great deal of growing up and a lot of effort to get us to where we are now, but the major piece of advice I’d give myself at that age would be to grab a good thing when you see it and don’t let go. Back then, I moved across the country and left him behind. A lot happened during that time for both of us, but we were lucky enough to get a second chance.”
– Lowrey Raines, 31, Los Angeles, CA
4) Celebrate how you feel about your mate
“One thing I’d tell the younger version of me is that there comes a time in every man’s life when you look at the woman you’re dating and realize that she is the single greatest thing that’s ever happened to you. And when you do, don’t be afraid to tell her and let others know how you feel, too. Trust me, she will appreciate it. I married the girl of my dreams, and not one day goes by without me thinking that she’s the best and most beautiful woman I ever met.”
– Richie Frieman, 32, Baltimore, MD
What people in their 40s wish they’d known while dating in their 30s…
1) That “must-have” checklist is keeping you from The One
“Here is what I wish I could have told myself 10 years ago: Get rid of your checklist of what you think you want [in a partner]. You don’t always know what you need. At the age of 38, I made a commitment to myself that I would throw away my checklist of what I thought I wanted in a man and open myself up to dating men of all types. That year, I received an email from a man on Match.com whom I’d gone on one date with three years prior; he had called me the next day to follow up, but I never called him back. He just wasn’t my type — or so I thought. Three years later, there he was, asking me out again. Because of my newfound outlook, I accepted. Nine weeks later, he proposed!”
– Lori Bizzoco, 42, Oceanside, NY
2) Realize that “boring” isn’t always bad
“I would have told myself to find someone boring! Of course, I wouldn’t have taken that advice. Unfortunately, I needed to date a psychopathic person first in order to realize the shrewdness of that suggestion. Fortunately, when I was finally given that advice by someone, I was also ready to hear it. It came from a younger friend of mine who was happily married. I listened to her, and now I’m happily married, too. And no, my husband isn’t boring — it’s just that sane people are boring by comparison.”
– Jen Hancock, 46, Tampa, FL
3) After getting your heart broken, you will meet someone else
“If I could, I would go back and talk to myself during the single darkest period of my life. Someone I loved very much decided she didn’t want me anymore. We broke up, and I entered a deep depression that lasted half a year. What I would go back and tell myself then is this: ‘This pain you feel now will end. And although you may not believe it now, you’re just six months away from feeling better, and you’re only a year away from meeting someone fantastic and you will find great happiness together. Time really does heal all wounds.”
– Scott Thompson, 44, Hatfield, PA
4) Don’t bother staying in a drama-filled relationship
“My advice to my younger self is this: If the relationship isn’t working and there’s a lot of drama after a year, then you need to let it go. I kept telling myself that relationships were work and that bumps were to be expected. I realize now that it shouldn’t have been that much work — or so bumpy. I stayed in it off and on for 12 years, and it’s one of my biggest regrets. I guess I’ve come to the conclusion that life is too short to feel so stuck, and I don’t have the patience for all that turbulence.”
– Dawn Quiett, 42, Dallas, TX
What people in their 50s wish they’d known while dating in their 40s…
1) Don’t jump from one marriage to another
“When I was 40, I re-married way too soon after getting my first divorce. I wish I could go back and tell myself that I’d grow into a much stronger woman had I not been so afraid to be alone. Having a man willing to rescue me felt so great at the time, but I wasn’t really in the best place to see him (or myself) clearly. This set me up to continue abdicating my power to a new husband. Instead, I would give myself a big hug and say, ‘Baby, wait until you’re strong enough to want a man. Never choose a man when you think you need one.’”
– Janice Christopher, 50, New Haven, CT
2) Maintain your platonic friendships
“I became a widow in my early 50s and was so glad that I had kept up with my networking skills and my list of work-based and personal contacts. When I found myself ready to date again, these people were more than happy to set me up with someone who turned out to be one gem of a guy. You know that good friends or family are not going to set you up with a jerk. Maintaining those relationships is hard work and can be a job in itself, but life happens — and it was so advantageous for dating again.”
– Luann Alemao, 55, Cedar Falls, IA
3) Use caution if you have conflicting ideas about kids
“Be cautious of single women in their 30s; they may only want an ATM and a sperm bank. Instead, consider dating women in their early 40s. In general, they’re sincerely looking to be in a relationship. Regardless of their stage in life, though, take your time, and look for something that meets both people’s needs, hopes and desires.”
– Ken Miller, 56, San Jose, CA
4) Interested men love the thrill of the chase
“I would tell my younger self quite a few things. First, don’t try to marry a man for his money — or you’ll wind up earning every penny of it! And if a guy isn’t chasing after you, forget him. Men like to be the ones who make advances and do all the chasing. Even if you are interested in him, make him think that you aren’t as available as you really are for dates. The old-fashioned advice about playing ‘hard to get’ actually has some truth to it.”
– Stella Vance, 56, San Diego, CA
5) Always trust your gut
“I would advise my forty-something self to jump in and fearlessly follow her heart. And I did, in spite of some details that could have easily been early deal-breakers (he was basically homeless and jobless at the time) for any relationship. After 2.5 years, my partner died suddenly — literally ‘dropped his body’ while dancing to a song called ‘Love and Happiness’ by Al Green. But the time we had together was one of the most profoundly meaningful relationships of my life.”
– Ishwari Sollohub, 56, Santa Fe, NM
What people in their 60s wish they’d known while dating in their 50s…
1) Date someone your own age
“In my 50s, I learned that dating women close to my own age worked best. Not having to explain the world I grew up in made connecting with them easier and more meaningful. I didn’t need a young woman to make me feel good about aging. Women who were youthful in spirit made it easy to overlook wrinkles. (I had them, too.) I worked hard to stay in shape, so I focused on finding a woman who shared that passion — and soon met my wife, who’s just a year younger.”
– Ken Solin, 62, Mill Valley, CA
2) Date around to figure out exactly what you want
“The best piece of advice I would offer up is this: Date far and wide, and do not stop dating too quickly! I should have dated more, but had a high school boyfriend and got married after graduation. I didn’t know myself and my desires and goals very clearly at that point, and knew I had to divorce him after five years. Get to know yourself and your goals very well before you commit to one person for the rest of your life. That’s something I did more of after my divorce. I have been married now for 28 years.”
– Sharon Gilchrest O’Neill, 62, Mount Kisco, NY
3) Don’t assume either of you will change once you’re in a relationship
“Never go into a relationship based on ‘potential’ that you’re confident you will be able to help ‘grow’ and ‘develop’ into something more. It’s much easier to buy into a person that’s already put together a life, like a well-assembled product. While no relationship can exist without a degree of compromise, we must never settle for less than what we deserve in terms of a partner having his/her own character and personal values.”
– Edie Raether, 68, Charlotte, NC
Judy Dutton (judy-dutton.com) is the author of Secrets from the Sex Lab and Science Fair Season: Twelve Kids, a Robot Named Scorch…and What It Takes to Win.
“I am currently planning my wedding with someone I recently reconnected with after 10 years: the bartender who made me drinks on my 21st birthday. It took us both a great deal of growing up and a lot of effort to get us to where we are now, but the major piece of advice I’d give myself at that age would be to grab a good thing when you see it and don’t let go. Back then, I moved across the country and left him behind. A lot happened during that time for both of us, but we were lucky enough to get a second chance.”
– Lowrey Raines, 31, Los Angeles, CA
4) Celebrate how you feel about your mate
“One thing I’d tell the younger version of me is that there comes a time in every man’s life when you look at the woman you’re dating and realize that she is the single greatest thing that’s ever happened to you. And when you do, don’t be afraid to tell her and let others know how you feel, too. Trust me, she will appreciate it. I married the girl of my dreams, and not one day goes by without me thinking that she’s the best and most beautiful woman I ever met.”
– Richie Frieman, 32, Baltimore, MD
What people in their 40s wish they’d known while dating in their 30s…
1) That “must-have” checklist is keeping you from The One
“Here is what I wish I could have told myself 10 years ago: Get rid of your checklist of what you think you want [in a partner]. You don’t always know what you need. At the age of 38, I made a commitment to myself that I would throw away my checklist of what I thought I wanted in a man and open myself up to dating men of all types. That year, I received an email from a man on Match.com whom I’d gone on one date with three years prior; he had called me the next day to follow up, but I never called him back. He just wasn’t my type — or so I thought. Three years later, there he was, asking me out again. Because of my newfound outlook, I accepted. Nine weeks later, he proposed!”
– Lori Bizzoco, 42, Oceanside, NY
2) Realize that “boring” isn’t always bad
“I would have told myself to find someone boring! Of course, I wouldn’t have taken that advice. Unfortunately, I needed to date a psychopathic person first in order to realize the shrewdness of that suggestion. Fortunately, when I was finally given that advice by someone, I was also ready to hear it. It came from a younger friend of mine who was happily married. I listened to her, and now I’m happily married, too. And no, my husband isn’t boring — it’s just that sane people are boring by comparison.”
– Jen Hancock, 46, Tampa, FL
3) After getting your heart broken, you will meet someone else
“If I could, I would go back and talk to myself during the single darkest period of my life. Someone I loved very much decided she didn’t want me anymore. We broke up, and I entered a deep depression that lasted half a year. What I would go back and tell myself then is this: ‘This pain you feel now will end. And although you may not believe it now, you’re just six months away from feeling better, and you’re only a year away from meeting someone fantastic and you will find great happiness together. Time really does heal all wounds.”
– Scott Thompson, 44, Hatfield, PA
4) Don’t bother staying in a drama-filled relationship
“My advice to my younger self is this: If the relationship isn’t working and there’s a lot of drama after a year, then you need to let it go. I kept telling myself that relationships were work and that bumps were to be expected. I realize now that it shouldn’t have been that much work — or so bumpy. I stayed in it off and on for 12 years, and it’s one of my biggest regrets. I guess I’ve come to the conclusion that life is too short to feel so stuck, and I don’t have the patience for all that turbulence.”
– Dawn Quiett, 42, Dallas, TX
What people in their 50s wish they’d known while dating in their 40s…
1) Don’t jump from one marriage to another
“When I was 40, I re-married way too soon after getting my first divorce. I wish I could go back and tell myself that I’d grow into a much stronger woman had I not been so afraid to be alone. Having a man willing to rescue me felt so great at the time, but I wasn’t really in the best place to see him (or myself) clearly. This set me up to continue abdicating my power to a new husband. Instead, I would give myself a big hug and say, ‘Baby, wait until you’re strong enough to want a man. Never choose a man when you think you need one.’”
– Janice Christopher, 50, New Haven, CT
2) Maintain your platonic friendships
“I became a widow in my early 50s and was so glad that I had kept up with my networking skills and my list of work-based and personal contacts. When I found myself ready to date again, these people were more than happy to set me up with someone who turned out to be one gem of a guy. You know that good friends or family are not going to set you up with a jerk. Maintaining those relationships is hard work and can be a job in itself, but life happens — and it was so advantageous for dating again.”
– Luann Alemao, 55, Cedar Falls, IA
3) Use caution if you have conflicting ideas about kids
“Be cautious of single women in their 30s; they may only want an ATM and a sperm bank. Instead, consider dating women in their early 40s. In general, they’re sincerely looking to be in a relationship. Regardless of their stage in life, though, take your time, and look for something that meets both people’s needs, hopes and desires.”
– Ken Miller, 56, San Jose, CA
4) Interested men love the thrill of the chase
“I would tell my younger self quite a few things. First, don’t try to marry a man for his money — or you’ll wind up earning every penny of it! And if a guy isn’t chasing after you, forget him. Men like to be the ones who make advances and do all the chasing. Even if you are interested in him, make him think that you aren’t as available as you really are for dates. The old-fashioned advice about playing ‘hard to get’ actually has some truth to it.”
– Stella Vance, 56, San Diego, CA
5) Always trust your gut
“I would advise my forty-something self to jump in and fearlessly follow her heart. And I did, in spite of some details that could have easily been early deal-breakers (he was basically homeless and jobless at the time) for any relationship. After 2.5 years, my partner died suddenly — literally ‘dropped his body’ while dancing to a song called ‘Love and Happiness’ by Al Green. But the time we had together was one of the most profoundly meaningful relationships of my life.”
– Ishwari Sollohub, 56, Santa Fe, NM
What people in their 60s wish they’d known while dating in their 50s…
1) Date someone your own age
“In my 50s, I learned that dating women close to my own age worked best. Not having to explain the world I grew up in made connecting with them easier and more meaningful. I didn’t need a young woman to make me feel good about aging. Women who were youthful in spirit made it easy to overlook wrinkles. (I had them, too.) I worked hard to stay in shape, so I focused on finding a woman who shared that passion — and soon met my wife, who’s just a year younger.”
– Ken Solin, 62, Mill Valley, CA
2) Date around to figure out exactly what you want
“The best piece of advice I would offer up is this: Date far and wide, and do not stop dating too quickly! I should have dated more, but had a high school boyfriend and got married after graduation. I didn’t know myself and my desires and goals very clearly at that point, and knew I had to divorce him after five years. Get to know yourself and your goals very well before you commit to one person for the rest of your life. That’s something I did more of after my divorce. I have been married now for 28 years.”
– Sharon Gilchrest O’Neill, 62, Mount Kisco, NY
3) Don’t assume either of you will change once you’re in a relationship
“Never go into a relationship based on ‘potential’ that you’re confident you will be able to help ‘grow’ and ‘develop’ into something more. It’s much easier to buy into a person that’s already put together a life, like a well-assembled product. While no relationship can exist without a degree of compromise, we must never settle for less than what we deserve in terms of a partner having his/her own character and personal values.”
– Edie Raether, 68, Charlotte, NC
Judy Dutton (judy-dutton.com) is the author of Secrets from the Sex Lab and Science Fair Season: Twelve Kids, a Robot Named Scorch…and What It Takes to Win.
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