XOXO Leah: Dating Older Men

Advice on relationships

By Leah Keith

Cover photo: Lana Del Rey surrounded by older men’s hands photographed by Timothy Saccenti for the August 2017 issue of Complex magazine.

Hey Leah!

I know this sounds strange, but I worked at a golf course this summer and long story short have been seeing a soon-to-be fifty-five-year old (he’s a pisces!) for almost 5 months. I haven’t told any of my friends on campus because I’m scared they’ll judge our relationship, even though I don’t judge theirs. He wants me to go to dinner and meet his kids. I’m not sure what to do. His oldest from his first marriage is about to be 24 (he’s an aries). His other two are still in high school. I am worried about what to talk to them about, and what to wear. He is suggesting Barbette’s in the cities. I don’t want to disappoint him because he is driving out with all the kids from our hometown (over two hours away), but I’m really nervous. I don’t know how to make the right impression, I want them to know I’m serious about their dad. How can I make the best impression possible?

xoxo,

a confused first-year

Dear a confused first-year,

Thank you for writing in with this story. I know it can be difficult to open up about relationships with strangers, but I hope I can be of help. Since we are both around the same age, maybe I can guide you in the right direction. I know you wrote in asking for advice on making a good first impression on your partner’s kids, but I am going to diverge from that part of your question a bit and focus on your relationship as a whole.

Before jumping in, I want to emphasize that I am always here to offer a sympathetic ear to people who are struggling with uncertainty in their life. You mentioned worrying about your friends judging your relationship, and I hope you do not find this message to be judgmental, but here are my thoughts and advice.

Although I will always advocate for respecting a women’s sexual agency, I believe it is still important to critically look at any relationship you are in. Think to yourself, “Why would a 55-year-old want to date a teenager?” When I first read this submission, I immediately thought of my favorite substack writer, Rayne Fisher-Quann, and her essay about dating older men titled “the pain gap.” Fisher-Quann discusses her experience dating men in their early-to-mid 20s as a freshly 18-year-old, and I think you could benefit from reading this essay. One quote that resonates with me goes: 

“they [older men] want a woman who looks like a baby but knows not to cry; a girl who’s mature enough to date older men but not mature enough to know why she shouldn’t. they want you to be cloyingly, lovingly childish until, suddenly, they don’t.”

The substack essay, with the caption, “on dating, maturity, and the benign psychohorror of womanhood.”

Many young women in the comment section of that essay share their experience dating older men, and you might find it valuable to hear directly from them, as I have never dated someone much older than myself. Additionally, I thought it would be beneficial to hear from Dr. Jocelyn Stitt, a women’s studies professor and the division chair of social sciences at St. Kate’s. During my conversation with Stitt, we talked about how this type of age gap often has an unequal amount of life experiences between the older and younger partner.

“There is usually a power imbalance in terms of life experience, as well as potential imbalances in finances, education, access to resources, as well as previous experiences in dating and relationships,” Stitt says. “In terms of intimate-partner violence, having a power imbalance could mean it is easier for the younger partner to be abused and to feel like they can't tell friends or family about their relationship, much like the writer of this letter.” 

As someone around this man’s age with kids of her own, Stitt cannot even imagine dating an 18- or 19-year-old. Even my older sister, who’s 23 and out of college, cannot imagine dating an 18-year-old. The life experiences between older and younger adults are just so incredibly different. However, Stitt mentions that in this type of age-gap relationship, we must place the accountability on the older person, who should know better than to be dating a teenager over 30 years his junior.

“A much older person pursuing a relationship with a younger person might not be able to date their same-age peers because women with more life experience might be able to see through some of their questionable behaviors,” Stitt says. “A much older person might also be pursuing a relationship where they want the younger person to have a kind of hero worship for them, or to depend on them in ways that might not promote independence.”

Furthermore, men that date younger women are often insatiable, as they often leave their girlfriends for even younger women. I mean, look at Leo DiCaprio and his inability to date women over the age of 25! Again, I want to respect your sexual agency, but I also do not want you to get hurt. I know this probably is not the advice you were looking for, but I still hope you find value in my response. At the end of the day, I cannot tell you what to do, but I will leave you with this: Stream Taylor Swift’s “All Too Well (10 Minute Version)” and then see how you feel about your relationship. 

Remember, the decision of who to date is only yours to make. I wish you nothing but the best of luck, confused first-year, and I know you will do what’s best for yourself. Sending you my love and well wishes,

xoxo Leah