I was answering a couple of questions about dating on my podcast yesterday and one of the questions was from a girl who has always been a supporter of mine.
I didn’t expect this question from her but it also made me realize this is a very common situation not just in America or India but pretty much everywhere. So I thought I’d list out my thoughts.
Should you date someone older than you? I personally believe it’s fine to date someone older, as long you’re very honest WITH YOURSELF about the pros and cons of doing so. Usually, anything more than a 7 year age gap will mean that you’re at very different places in life. This can cause long term friction in relationships.
This is my just my experience so I thought I’d explain a lot more details and examples of what I mean. If you’re dating someone and have a different experience please let me know in the comments. And if you’ve already started dating someone older and are hopelessly in love, well…good luck.
Should You Date an Older Guy?
Well, it depends. What’s important to you?
I grew up in the online dating world of Match.com and OkCupid and then witnessed the Tinder and Bumble generation when I had some bit of maturity about the opposite sex.
I know the apps have really changed the rules of dating and part of that is we really just swipe on a person’s highlight reel, not the behind the scenes which is the real version of their personality.
Seeing a 35 or 40-year-old dude who flies planes, has a boat, is in good shape, killing it at his career and/or rocking the salt and pepper hair (hey there) can be enticing and also welcoming from the younger non-commital culture.
Benefits of Dating an Older Man
It’s nice to know someone has their stuff together and if you’re 22 or 30 and see someone in their 30s or 40s, they’re a lot of pros to dating an older dude. Specifically:
- They’re usually done screwing around.
- They will have their career and finances sorted.
- They know what they want. (well, maybe)
- They recognize their metabolism has slowed down so they’re active.
- Most are a lot more accepting of marriage in their 30s (or 40s) than they would have been at 27.
Cons of Dating an Older Man
Of course, all the pros of dating an older dude also have some negatives.
One of the hardest parts for guys of all ages, at least with long term dating or marriage is not the marriage itself…it’s just learning how to not be single.
We grow up so used to figuring our own meals, lazing around letting things be a little dusty, forgetting to call back or make plans that many times this can be unsettling for a long term partner. Now imagine all of that PLUS an 8-10 year age gap, and they’re a few cons to dating an older dude.
If you’re a 24 or 25-year-old girl who still wants to go clubbing every weekend, go on an excursion filled holidays to Bali or Thailand, want to spend the whole night in the you know what or simply talk till 2am…you also have a lot to think about:
- They’re done with the wild birthday nights and after-parties. They wanna go home by 11 and watch Netflix or do stuff on their laptop.
- He doesn’t want to travel every free moment or go to brunch every Sunday.
- Might have ex-wives or kids or other baggage you may find difficult, even if you think it’s mature to just deal with it.
- Usually pretends to be more outgoing and energetic than he actually is.
- Pretty set in his ways after 30+ years of doing so (food, health, alcohol, job, entertainment, etc…)
- Probably one and done in the “you know what” department.
I’m not saying dating an older guy doesn’t work. I’m just saying don’t think that if you’re 22 and a 35-year-old wants to marry you, when you’re 27 and he’s 40 that there won’t be minor hiccups.
- Maybe on your 27th birthday, all your girlfriends want to go to Vegas or Goa and he can’t or won’t.
- Maybe you were pressured to have kids too soon (or maybe it was perfect for you) and feel you compromised too soon.
- Maybe he wants to whisk you away to another country forever while you still want to do that masters program at home.
- Maybe you still like ordering in while he likes to cook at home and expects you too also…who really knows?
You just need to know what you’re sacrificing or compromising on, which is usually going to fall on the younger partner because usually an older guy or girl won’t take a younger person’s problems as seriously because they’ve moved on from that phase. (e.g. bachelor parties, office functions, whatever).
Tips on Dating an Older Guy
If you’re dating or married to someone at least 6 years older, there are a few tips you should know about all of us, from 25 to 50.
1. We’re not as busy as we’d have you believe.
Just like a 25-year-old looked like this super fancy dude when you were 19, a 35-year-old is the same immature person, just with a bit more money.
So if you’re 27 and your 35-year-old dude is saying he’s tired, or doesn’t have the time (yet is pretty active on Instagram), just know for those people who are serious about their relationships…there is always time. Call them on their bluff and watch them sheepishly agree or laugh and say “ok let’s go meet your friends.”
2. Set expectations from the get to.
It’s nice to date someone older because they ground you in what’s important. Spending quality time or not going out every Friday is a good thing.
Later, even though he didn’t do it at your age, you might be glad you had kids at 29 versus 36.
But I would say at the very least if an older guy wants to date you seriously or long term, make sure you’re vocal about your wants, desires, and expectations.
Express your hesitations and hold them accountable. “I told you my friends 25th birthday is important and we have to go, now why are you being a jerk and saying you want to stay in, etc…”
And if your parents express their doubt, it’s not bad parenting, it’s just being cautious.
3. Excess Baggage is well, extra.
I don’t care if you’re 1 pound over or 10, those airlines are going to get you to pay. And usually, if you pay for one pound, you’re paying for an extra suitcase. In the same way, if your older dude has kids or an ex-wife or (yes, very common) still married and said he’s “working on a separation,” well, trust me…this issue can and will come up.
I know you say you’re “so chill” and it’s going to be fine, but I have seen girl friends of mine make these mistakes time after time because they had wishful thinking about a lot of this stuff.
A lot of older guys are just lonely in whatever phase of divorce or late 30s they’re in and they’ll probably tell you their baggage isn’t over the weight limit because well, that’s how you board the flight and get to where you’re going.
Now for the young chaps…
Should You Date Older Women?
Well, how much older is she?
A lot of young guys like to joke about cougars and “Bro, she’s like 34, she’s so wild bro, she knows things” and all of that.
But a lot of those same guys are just all macho talk and want the companionship and sadly, need to be babied and looked after.
Regardless, if you’re a 22 to a 30-year-old man and you’re seeing (or will see) someone older, then you should weigh the pros and cons as well.
Benefits of Dating an Older Woman
Older women are usually more clear about their lives and what they want and when they want it.
Sure some 30 something women drift around in Goa or shun corporate life while not doing anything else as an alternative. However, compared to SOME 22-year-olds who are just confused and pick a grad school mindlessly or take whatever job they can, older women, for the most part, are trying to line things up for the long term.
Usually, if you’re dating a woman that’s 5 to 10 years older than you, the benefits include:
- Less silly games and jealousy that we all suffer from in our youth.
- Working professional that has chosen a direction.
- Probably enjoys chilling at home rather than going out all the time (if that’s you too).
- Enjoys things like hikes, gym, parks, movies as opposed to bars and clubs and holidays.
- Probably has a dog or a cat (hopefully you do too?).
- They will give you a good mature butt kick to get your life in order (e.g. finances, health, friends, etc..)
Cons of Dating an Older Woman
As usual, let’s start with the obvious.
And again, these are from a younger guy’s point of view, not from a similar like-minded 34-year-old guy.
- Girls between 28 and 35 usually want to make sure this is going to end in marriage, where you might just think this is a 1-2 year fling.
- The ticking clock for kids is an added pressure.
- Chances are, you’ll have large financial differences which may or may not cause issues. (buying or renting a house, travel, personal tastes, etc…)
- May expect more out of you than bars and Netflix (e.g. more meaningful conversations).
- May not 100% communicate what is really important to her with the hopes that you’ll want to settle down, then simply waste another 2-3 years.
Tips on Dating an Older Woman
If you’re a 22 to 25-year-old man and seeing a girl in her thirties or forties, here’s some guidance for ideally both of you.
1. She Probably Wants To Get Married, Even if She Says She Doesn’t
I’m not saying she wants to have kids or marry you tomorrow, but unless she’s divorced with kids and not looking to do all of that over again, chances are she wants to get some stability and move on to the next phase of life.
A lot of girls I know, again, will say one thing just not to scare off the younger dude they’re dating, but we all want companionship and usually, women are keener than guys to do that sooner in life.
So if you found yourself a nice cute sugar mama just make sure you’re honest with her that you plan to bounce in the next few years or this is just fun for you, because it’s not going to get any easier on either of you when you tell her you’re moving to Thailand at 27 when she’s 33 in the city.
2. Relationships Are Way More than Physical
When you’re 21 or 25 with a little bit of career swag, most guys just want to make up for lost time and try to hook up with everything that moves. This can be exciting if you start seeing someone older but trust me, it gets old fast.
I know it won’t make sense to your testosterone and Instagram model filled daily life, but if you don’t know this beyond three months of a honeymoon phase you’ll learn soon enough. Make sure if you are into someone much older it’s because they’re just the coolest person you’ve ever met, irrespective of their age relative to you.
3. It’s Ok to Man Up
A lot of guys will get high fives from their buddies when hooking up with an older girl, then also get called whipped or changed when they no longer come out every Friday, party less, or get caught making pasta on her Instagram story.
Your friends your age are going to continue to party away their 20s, so as long as you’re fine exiting that lifestyle, by all means, march on. Nobody ever says “I’m so glad I went out drinking on that pointless Friday night seven years ago” but people regret a lot of wasted time, all the time.
So if you find someone older who isn’t really changing you but just making you a better version of yourself, go ignore the noise and enjoy your life (and this is true for dating in general).
I know so many girls who stay in relationships after 30 that are clearly going nowhere, and instead of making a clean break and starting over, they double down and then are single again at 34.
I also know so many guys who date a younger girl thinking they can keep up, going back to their lazy comfy ways and then disappointing that person who’s just trying to revel in their youth.
Instead, I wish both of those girls and guys realized while yes it sucks to start over at 31-35 year of age, you’ll probably now have the skills to identify the right one a lot faster and make a better long term decision even if after dating someone for just a year or two in those later years.
You may not know what you want, but you’ll definitely know what you don’t want and that ends up taking you the rest of the way there.
Does that make sense?
It did for my parents and maybe yours too.
While dating someone much older in today’s digital world is personally not advised (by me), it’s just something you need to tread with caution in an already complicated modern dating landscape.
Plenty of people use less social media, are truly happy about their partner and life goals when younger, and put a determination towards their relationships that many of us don’t.
In fact, I ‘ve noticed that most of us who grew up in big cities are so confused, that in our 30s we realize the small-town folks who got married young had it right all along.
If you have that conviction and have very clear goals about what you both want…well, happy dating 🙂
Sanjay Manaktala is a stand-up comedian, author of the Harper Collins Book “My Beta Does Computer Things: You’re Guide to the IT Industry” and digital content creator. His latest effort is the Birdy Num Num podcast, helping you learn creativity in life after engineering. You can learn about Sanjay here or check out his stand up comedy YouTube channel here.