What It’s Like To Date Someone Older Versus Dating Someone Younger Than You

At 25 years old, I find myself with gray hair, a propensity to doze off in front of the news around 10 PM, and the general disposition of a man around 40 years my senior. Also, I’ve just started seeing a younger guy, which sort of completes my application to the Palm Beach Country Club.

He’s 22, and while those three years of age gap represent the least of any man I’ve dated, they make me the older man in the relationship, a concept as foreign and unexplored to me as stock trading or gardening.

I find myself questioning everything — am I supposed to pay for dinner because I’m older? Do I have to initiate sex? Do I have to pretend to like his music?

I’ve always been the younger man, the one expecting to be looked after and paid for. This past week I’ve rekindled a conversation with someone I met while visiting Miami at 22. He’s somewhere north of his mid-40s, and has offered to fly me cross-country to see him, stay at his beachfront condo, and be regaled like a prince. I am much more comfortable with this type of scenario, not because it’s happened many times (ever) before, but because in many ways I still don’t feel like an adult and this type of pampering/parenting feels natural.

Despite my predilection for bran cereal and prunes, I hardly feel grown up. Part of it is my lifestyle; I avoid responsibilities, I don’t have a savings account, and most days I wear a t-shirt if I bother getting dressed at all.

Dating someone even just a few years younger at this confusing juncture (as Britney summarily characterized it: not a girl, not yet a woman), makes me more conscious of my age, and my current standing in life. I feel like I want to pay for most things, and I want to impress him, but at the same time I’m hardly in a real position to do so. Moreover, I wonder if he’s hanging around only because he perceives my life as more gilded and glamorous than it actually is. While I have many outward appearances of a comfortable life, it’s as liable to collapse at any moment as an anorexic model at a SoulCycle class.

But mostly dating someone younger (even if it’s just a few years) has so far proven much easier and more pleasant than the inverse. During the weekend we spent together, the 22 year old was amenable to anything; he didn’t mind driving, he didn’t mind watching tennis, he didn’t mind playing gin rummy, he didn’t mind hooking up. After having hung out a few times with not so much as a flirtatious exchange between us, I asked him directly if he wanted to kiss or be friends (I actually asked this in French, so it sounded more like, Est-ce que tu veux qu’on s’embrasse ou qu’on soit amis?) He asked what I wanted, and said he was happy with either.

Since he’s so easy to be around and asks for nothing, I wanted to please him, to make him happy, the same way I feel towards my dog — which is probably the closest thing to love I’ve ever felt. Bringing him pleasure in turn made me happy. I feel protective towards him, in the way you can only feel when you’re in a position to either help someone or enrich their life in some way.

When I’m with an older man, it’s about what I want. I feel I am sacrificing something of myself (my dignity? my independence?) and in return I expect deferential treatment. Being that the men I’ve dated tend to be old enough to be my father, or at very least an uncle, I’ve had no problem treating them like one. My own father always paid for our meals, so why shouldn’t my new daddy?

More often than not, they are happy to oblige, and now I understand why. It’s the same desire to impress, to feel needed, to be looked up to so that the age schism represents wisdom and success instead of just wrinkles and a flabby waist. It’s why older men want younger women, it’s why they say it’s better to give than to receive, it’s why I think I want to be the older man.