Print Friendly, PDF & Email

Why should you start dating a younger man? Silver haired foxes and crotchety middle-aged men are good for lots of reasons: replacing light bulbs, going to the park, walking dogs, and yelling at teenagers.

But if you find yourself recently single and…say you’re a lady who’s hitting the dreaded fortyish zone…you know the one where you start to become invisible?

Here are three important reasons why you should start dating a younger man right now.

For starters you won’t feel invisible anymore. Also, the fact that doors aren’t being held open for you as quickly as they once were won’t bother you as much.

Reason No. 1: A younger man is eager to please.

Now I’m not saying he’s going to call you Mistress and lick your Louboutin’s (unless you want that) but a younger man (by sheer limited number of years on the planet) usually has less experience than an older man.

Keep this in mind when you are dating a younger man. He’s eager to find out what you like and wants to make you smile. It’s a crowning achievement for him if he can really make you laugh. So let him work for it.

This is your chance to be direct, Sally. Tell him what you like and more specifically what you don’t like.

Now here’s a small warning, don’t get mom-ish. You know what I mean. Don’t look at me like I’ve got a third eye. For god sakes woman, be gentle when you tell him what you don’t like.

He bruises easily.

You may find it repulsive when he jams his tongue in your ear like a bad version of Alien and he’s probably thinking it’s his rockstar move on your lady parts.

When dating a younger man ease him down gently, “You know Pedro, the tongue in the ear thing doesn’t really work for me (you’ve shifted the blame on you), but I really like it when you rub my elbows and suck on my finger.”

Again, I’m telling you be direct. This lover boy (nor any other) cannot read your mind.

Reason No. 2: His emotional baggage is carryon size.

Lady, I know you have issues. I’m right there with you. From ex-husbands’ bouncing around to mortgage payments to the fact that you keep gaining and losing the same 10 pounds over and over again. I get it.

Your boytoy doesn’t have those kinds of problems nor does he have the same frame of reference that your forty-five-year-old ex-husband has either.

You know the one where your ex-husband is damaged and disillusioned because his life and career didn’t turn out the way he wanted, and somehow you’re to blame?

You get a clean slate with your younger man.

I recently dated a younger man and as we were talking about our ex’s. We discussed my middle-aged ex’s erratic behavior. My boytoy looked at me and said, “He’s a creep. That guy is bullshit.”

And you know what? That simple, direct, and honest appraisal of my ex’s behavior pretty much did for me what analyzing years of his multi-faceted mind-games couldn’t.

It gave me a fresh perspective.

My boytoy was right and I’m not in the shit-taking business anymore. Less baggage equals more fun and that’s something you need in your life, right now.

dating a younger man

Reason No. 3: You’re attractive as hell to him, sexy, so work the Mrs. Robinson vibe.

Before you go second-guessing your looks and your sex appeal, I’m going to stop you right here. Let’s have a heart-to-heart, shall we?

Don’t make excuses for your body. Don’t wish you could get Restalyn injected in your smile lines before your next date.

Just don’t do it. Stop thinking about it now. If you don’t like the way your breasts look, go and get a sexy push-up bra that fits and hoist those girls up. You’ll feel remarkable and look ten pounds thinner. Leave it on during sex and disaster averted.

Ok, moving on.

This younger man is dating you for two reasons. First, he finds you sexy as hell and wants to get in your panties. (Newsflash: they all do.) Second, he enjoys your company.

Don’t screw it up by feeling insecure about your looks.

Looks are relative; a pretty face can only take you so far. You need the personality to go with it. And at your age you’ve got a fantastically well-developed personality.

You don’t have the insecurities of younger girls. You’re not clingy.

You won’t call him fifteen times a day to find out what he’s doing. You’ve got a life. You’ve got plenty of other interests that don’t involve keeping track of him. You’ve been around the block and back.

It’s your confidence that makes you appealing, not just your looks.

Own it, Sally.

I admit it sometimes the open admiration of a younger man about your beauty, your body, and other bits and pieces can be a bit disconcerting at times. But work it.Take every single compliment and reply with, “Thank you.”

That’s all. Don’t make excuses for anything.

You earned every stretch mark and bit of cellulite. Your thighs still work right? Those kegels you’ve been doing certainly help. You’ve earned the right to feel amazing in his arms. So shut that crazy insecure inner-voice down and let your inhibitions loose.

Early on in my relationship with my younger man, I was feeling particularly insecure about our age difference.

One night, over a several glasses of Malbec, I voiced my concerns and in another nugget of wisdom he said, “Who cares? Twenty-five and thirty-eight together is hot. But when I’m thirty-seven and you’re fifty…not so much.”

Here’s why I didn’t lose my shit in three seconds when he said this.

He’s brutally honest. I appreciate honesty and I’m sure you do too. Also he’s right.

The fact is, I don’t want to be a fifty-year old mom taking a crying child to kindergarten. That’s not happening. I’ve already been married. I’ve done that.

My boy toy hasn’t been married yet, so right now we are having a good time. I’ve told him marriage for me is off the table. For him marriage and children are something he’s looking forward to, eventually. So yes, right now it’s hot as hell.

But later on in life (even though I plan to age like Halle Berry and Demi Moore combined), I’m not going to repeat that part of my life again ever.

So I’ll enjoy our time together for now.

As time progresses and we part ways, I’ll remember him fondly.

And when he’s up at four o’clock in the morning and stepping on Lego’s in the dark, I’ll be in the south of France on a beach chair, watching a hot young waiter bring me Champagne.

About the Author Alexandra Andersen


I founded Wine & Drama to make you laugh and help you learn all about wine, food, and living well. I love stinky cheese, my Nespresso machine, Loire Valley white wines, bold full-bodied reds, and championing ladies in winemaking.

Get Your FREE Wine Cheatsheet NOW

>