Blind Dates Can Work. Men Like Walking. And Other Things You Learn When You’re Still Dating In Your Late 30s

Leonora and Eve Epstein are sisters with 14 years between them. So they've got very different views on dating

Rory-DCS

by Leonora Epstein and Eve Epstein |
Published on

Sisters Eve and Leonora Epstein may share a family connection, but that's really where the similarity ends because, with fourteen years between them, they may as well come from different worlds. Well, at least they come from different letters. Eve is a classic Generation X-er (those born between 1960s-1980s) and Leonora is a Gen Y-er (anyone born from early 1980s to early 2000s). As a result they have completely different opinions on what consitutes good fashion, music, TV and, yes, good dating. But what are the key differences?

In the Generation Y corner:

**Dating is a shit, but necessary, evil **

Millennial dating is rarely fun. And yet, it is an inevitable aspect of single culture. Unless, that is, you are a veritable hermit, which I’ve heard is an often preferable alternative and really not all that bad, providing you have Netflix and an ample supply of alcoholic beverages. But the fact of the matter is, we all need to get laid at some point. Or, beyond that, have someone around to take care of life’s less fun things such as taking out the trash and killing insects of both large and small varieties.

Social media is a minefield of potential cockups

Do not, no matter how skilled a stalker you are, presume to know someone before meeting them IRL. Yes, you might come across hints that would seemingly, undeniably indicate that this person is your soulmate — e.g., photos of a volunteer trip, an adorably geeky love for Captain Planet — but you never know how you’ll feel about a particular individual until you actually look them in the eyes and decide whether you’d be okay with this person seeing you naked. With that in mind, if I meet someone you like, I do not' 'friend' them in any way. I just don’t do it. We are not friends. Friends are made over years, months maybe. Not over £2 shots and a drunken makeout session.

Modern chivalry does not look like a Kate Hudson movie

If you feel like dismissing someone because he doesn’t open doors, does not plan elaborate dates filled with surprises, and does not pay for absolutely everything, you will spend a long time looking for that person. Times have changed. (I’m sorry.) But! There is still romance to be found in sweet emails/texts. Speaking of which...

Texting is both a blessing and a curse

It will probably be your primary mode of communication in the event that you and your prospective romantic partner decide to move beyond the first date. (Squee!) Although texting may seem far less romantic than picking up the phone, consider that it allows you time to craft witty, sexy responses largely crowdsourced from your two best friends and that one co-worker who is forced to listen to all your dating dilemmas. Of course, when the ball is not in your court, text messaging becomes an incredibly annoying and risky game. Keep messages brief, limit exclamation points, and only use the word “yolo” ironically.

Booty calls are very much a 'a thing'

If your romantic prospect texts you something to the tune of hey, sup?, or yo with no further information, this person wants to sleep with you but would rather not pay for your meal if it can be avoided. I’m sorry.

It's going to be OK

It’s easy to say that technology has made our love lives more confusing than ever. But consider the fact that you at least have access to so many more people. True, most of these people will torture you with their lackadaisical, non-committal, too-cool-for-school hipster bullshit. But then one day, one of them won’t.

In the Generation X corner:

**Dating younger men is a bad idea **

For GenYers, platitudes like 'age is just a number' and 'you’re only as old as you feel' begin to sound less like Lipitor ads and more like really smart words to live by. Go ahead, live by them — just don’t date by them. Don’t lie about your age and don’t imagine that anything good can come of dating people significantly younger than you. You’ll just end up hating them when they drag you to Bonnaroo and say things like 'What’s Watergate?'

**People have histories **

Dating when you’re older is sort of the opposite of modern air travel: The extra baggage comes free. If you’re Gen X and you’re single, you’re going to end up dating divorced people with kids. Don’t let this scare you. The truth is, young people have baggage too. They just have less self-awareness and wisdom about it.

**Blind dates aren't cringey - they're great **

Your friends think they know someone who might be good for you. What are the odds of that being a good idea? Very slim, to be sure. But not as slim as meeting someone suitable any other way. At least you have a friend or two in common, which is likely to be some indication of common interests or sensibilities. Also, don’t do that awful thing where you get mad at someone for setting you up with someone who’s 'not in your league.' Think about it for, like, four seconds: If they’re friends with that person, they probably think he or she is pretty great. So you’re just insulting everybody.

**Awful online dating profiles don't necessarily mean awful dates **

It is a truth universally acknowledged that a single GenXer, newly arrived on OK Cupid, will write something that sounds like a parody of a cheesy personal ad. Gen Y people approach the act of creating a social media profile as an intuitive extension of their identities—e.g., if a Millennial thinks of himself as funny and articulate, his profile will be funny and articulate. If a Gen Xer thinks of himself as funny and articulate, he will write, 'I’m funny and articulate!' and just expect you to take him at his word. You must look past this if you want to date.

GenYers LOVE walking

I don’t know about Gen Y, but nearly every Gen X guy I see on a dating app or website portrays himself as a rabidly passionate outdoorsman. Judging from these people’s self-reportage, they spend exactly zero hours a day indoors, preferring to do even their taxes at the summit of a just-scaled, snow-capped mountain somewhere in South America. On a date with someone like this, you can pretty much count on there being some sort of open-air 'adventure' in your near future, one that calls for flattering-yet-sporty attire. Plan accordingly.

Buy X vs Y here

Follow Leonora on Twitter @leonoraepstein

Picture: Rory DCS

This article originally appeared on The Debrief.

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