10 Reasons to Date a Younger Man

Written by Benscudder – Older Women and Younger Men Are Getting Together


  • The whole younger man/older woman scenario generally plays out better when kids are not involved
  • An older woman is much more tactful about traps and snares at big family gatherings
  • Younger guys have grown up in a world where women doing more, earning, being more, is commonplace

A good friend shared with me that his sister showed at Thanksgiving with a much younger man. This was the boyfriend nobody had met all year. While in theory many more people might accept this, it made for some awkward moments around the traditional bird.

After the initial shock wore off, he had his sister to lunch with us both. We talked candidly about the trend of more widespread acceptance of older women and younger men in relationships in today’s society. “Carol” wanted people to know she wasn’t being taken advantage of.

Carol had some pretty bald faced good reasons to be with a younger guy. The tables were turned, it seemed, on traditional relationships. Here are the “whys” I have come up with for why the older woman with younger man relationship will work out for some people.

1. Put Down the Scales.

Carol remarked that almost all her relationships in her 20’s and 30’s had been with men who were so competitive it exhausted her on too many levels. It felt as if too many of these older men viewed the entire relationship as some kind of a competition. Younger men her age were like this too.

Carol spent too many years “keeping up the appearance” of second place. If she achieved a benchmark or thought of something, hatched an idea or had a business success, her Significant Other couldn’t handle it and bruised her ego. Now she sets the pace and it suits her fine.

“Most men my age and older are too competitive, younger men don’t try it.” With a younger man Carol feels that her successes are celebrated with her in the spotlight she’s earned, instead of just marked on the scoreboard. Just being allowed to feel happy about her work makes a better relationship.

2. Most Men My Age are Married/Divorced with Financial Burdens.

Carol spoke of dating and being in relationships with men who had long tails of child support, financial settlements, alimony, and earnings reductions due to past marriages and relationships. This put a damper and a leash on whomever she was dating. And that was the healthy ones.

“I got tired of feeling like an outsider in my own relationships. It was always the right thing for the guy to do the wrong thing, rush off, get the kid that weekend. I was expected to date the kids! Forget it.” Carol acknowledged that the burden of the past was lighter with a younger man.

To Carol, most younger men don’t have these issues. “I am not competing with the ex-wife on the phone, setting my calendar and budget according to his divorce settlement and past, or outracing the kid’s needs for attention. That goes a long way.”

3. Most Younger Men appreciate my Experience.

Carol mentioned that she had a lots of professional mileage and that this made life easier on the younger man in her life. She knew her way around the block. Instead having to call a friend or mistakes in business, she knows the ropes. Carol’s boyfriend enjoys a leg up in his everyday professional life.

“It’s like a being a business friend with benefits, but I won’t eat the last slice of pizza or the last beer”. Or steal his job. Carol’s knowledge and guidance as an attorney was weighed versus older men who stubbornly head into disaster to “prove a point”. Carol had dated a divorcee who nursed a grudge against his first wife’s business decisions with their money. It never ended.

Carol cites her dilemma with men closer to her own age: “I got tired of fighting a battle for supremacy everyday. It was too mean spirited. I have abilities and skills and I got fed up trying to pretend I am less than I am. An older guy is immediately threatened by that, because he hinges all his superiority on being able to do more, even when he can’t.”

According to Carol, younger guys have grown up in a world where women doing more, earning, being more, is commonplace. They accept that a women can be competent in areas that they are not. “There always seemed to be a vanishing point where I was supposed to quit and have kids and get married, or hit a plateau and the guy’s career was more important.

4. Show Me The Money

Carol spoke of a man she had moved in with in years past. He had lost all his money in investments and these fears governed their entire combined money matters and leisure life. “Money hung over us like a Damoclean sword. Every day. It was wearying to live like that.” Carol knew another man with these problems. “It was like a timer was on the relationship with money attached to it”.

In her current relationship, Carol manages the money, to a point. “I pay the mortgage, and the insurance payments. He handles the food and extras. In terms of time and management, it’s worth it to me. Our play time is in the clear, not paid for on credit or spent hiding from obligations.”

Carol also cites better R & R. “I like that when we look at vacations, there are no golf balls in sight. If I want to backpack or take a drive, the cell phones get turned off. There is no business priority outweighing our time together, unless I put it there.” Caril recalled her boyfriends having high-priced toys sitting in storage while she budgeted pennies.

4. Alone Time is Premium

Anybody who knows Carol knows she is independent to a fault. Carol explained how she and her boyfriend structure alone time to pursue friendships and other interests so that time can never be unevenly spent out of whack.

“If I come home from business meetings since dawn and the condo is dirty, yeah I’m a little angry. But if he wants to check out the museums and exhibits, more power to him.” Carol acknowledges the division of labor at home can be tricky. “But I saw too much of what I didn’t want to be in relationship to make someone else do it”.

“I always think of what my life would have been like if I had had a relationship at an early age with an enabler, instead of a daddy-type or corporate glyph.” Carol had too many relationships that did not make her happy to let another one commence without having some ground rules.

5. Maturity, Maturity, Maturity.

After their first argument, Carol went to bed and asked if they could talk about it in the morning. Her boyfriend was stunned. His old girlfriend, Carol explained, would have been huddled in the bathroom with her mom, dad, sister, or college roommate on her cell phone for hours.

When his job got cut to part-time Carol shrugged and rearranged the chores. No crying, screaming or worrying. “The goal is to keep things stable. I always wanted more stability in the home life but it was always touch and go every day with the big man’s job or career. A few dollars more doesn’t really matter”.

Carol learned that a lot of her hard-won experience in relationships paid off with a younger guy. His friends can’t sabotage the relationship because it’s out of their peer group. Maybe he didn’t have all the tools to work out a disagreement. Maybe he didn’t know how to act. “The Midlife Crisis is so much farther away for these younger guys, They are much calmer”.

6. Meeting The Family

Carol says the key to meeting the family of a younger guy when you are an older woman is to treat it like a business meeting. “Don’t let your guard down, don’t let your feeling hurt, don’t be disrespected. “Make the people work for you to like them, not the other way around.

Carol says it was freeing to not have to live up to the perfect college girl or debutante stereotype and deal with being his Mother’s “dream girl”. Carol says family get-togethers give big clues to an experienced woman what kinds of emotional needs a younger man is dealing with.

“Where he spends his nights is already decided before we get there. If his mother wants to bring it out with the fried chicken and macaroni salad, it says more about her than me”. Carol says family meets can yield unexpected family allies who have previously taken a back seat in the younger guy’s life.

“I went to a pool party for one guy’s family, I think they spent their whole time blinking hard in my face. But I saw what he was up against, a very macho bunch of brothers who didn’t respect his feminine side at all. He’s an artist now, I connected him all over the place. ”

Carol says an older woman is much more tactful about traps and snares at big family gatherings. “They spent the whole night trying to belittle me and it didn’t work. I could have bought and sold many of them. They looked small and it showed. ” Carol says that it’s easier to deal with family issues when you are on the outside.

7. What About the Future?

“One former boyfriend practically had his entire life run by his older brother. I hated that guy. He was bent somehow. When Pablo moved in with me, he learned how to speak English better, got some college, and found his own job away from the family company. They got sued later and all lost their jobs, but Pablo was better off elsewhere.”

While Carol says not every relationship lasts, the time spent together is much more fulfilling than relationships with older men. “They just stop giving at a certain point. It’s an uncomfortable slant. Now I have a choice”. Carol says most of her married friends get divorced anyway.

Carol likes to get it in writing what expectations are on both sides and then make sure that legal agreements keep them both covered. “Then the relationship hangs on its own weight”. Breakups are emotionally painful, just the same. But not as bitter, Carol insists. There are no “best years of our lives” type mud-slinging.

8. Easier Without Kids

Carol admits the whole younger man/older woman scenario plays out better when kids are not involved. “I never wanted kids, and don’t misrepresent that to my partners”. Carol confesses she would be much more restricted in her choice of relationships if either the man or she had children.

“I don’t infantilize either one of us. I just don’t want kids and don’t want the man to believe in any way that’s just “in my head”. Carol thinks from what she has seen men want to pressure women to have kids even when it doesn’t make sense. Especially older men, who are more used to having their own way.

“I still don’t want kids. When I was in my 20’s men would just smile when I said that. Now they are trying to figure out how to pay the bills and where the college money is coming from. ” Carol says younger men are not as hell-bent on having kids right away. That suits her just fine.

9. The Social Aspect

Carol describes what kinds of resistance she gets from her boyfriends about attending black-tie events. “Most of them think of anything to get out of it.” Scrutiny about the relationship foams over at corporate or public outings, but social events can become a pressure cooker.

“I am very popular when the company volleyball league starts up every year”. Carol recites past accounts when wives of her business colleagues have gotten too friendly or put their feet in their mouth. “You do become the focus of a lot of attention. But then the same people who stare resent you for hanging out for shock value!”. But Carol cites that her partners have survived the duration of many couples at these events.

10. The Eye of the Storm

Carol has observed that the strength of any younger man/older woman relationship she has had is the feeling between the two principals. Feelings, instead of programming, drive the commitment. She feel that her choices were much more limited when she was younger.

She feels that when women are younger in our culture they are much more guided by a societal idea about what relationships and marriage are supposed to be, and can’t really speak yet as to what they want. “And until they start making more emotional choices, they’ll fall into the same societal expectation of a relationship with an older man”.