Flash Friday: What’s the Hardest Part of Dating Now and Then

Today is Flash Friday – when 40:20 Vision tackles an issue from both the 40-something and 20-something perspective. Joining me on this mission is Molly Ford of Smart Pretty and Awkward. For this month we put out the question to the twitterlands — what topic do you want us to take on?  The answer — dating. It must not be obsolete because it wasn’t how to date or get a guy to ask you out but rather more a curiosity over what others find hard about dating today vs. 20 years ago.  It’s a classic case of “you are not alone”.   Here with the perspectives.


The 20-Something Perspective 

By Molly Ford

Whether you go on dates 6 out of 7 nights a week or haven’t dated in many years, everyone has both awesome stories and less great stories from dating. But overall, why is it so hard to date in your 20’s? Current 20-somethings weigh in on what the hardest part of dating today is.


Is it an issue of time and priorities?

“There is so much a 20 something has to do to invest in their future and it is SO hard to find the time to dedicate to dating. Personally, so many of my first dates are not with the guy I am looking for, so it continues and I have to keep setting aside time to invest in dating.”


“Balance: Spending time with your friends/family, his friends/family, and spending time (alone) together.”


Is an issue of background checks?

“Without having mutual friends, it’s hard to get a sense for someone’s past; both childhood and old relationships. Prying comes off as desperate and needy, but not asking can be a lot worse.”


Is it deciding when to pursue something and when to retreat?

“The hardest part is figuring out if you should pursue further dates or break it off– and then. Figuring out how to do that.”


Is it something technology-related?

“It’s the text messages that kill me. I spent all day or all week post-a-good-date staring at my phone hoping to see a text. It is seriously annoying and seriously mentally draining.”


Is it aligning values?

“Finding a decent man to date. Few men have the values women crave to settle down with in their 20’s.”


Is it simply finding someone to go a date with?

“Actually meeting people is by far the hardest part of dating.”

(This answer was given to me multiple times!)


Is it decoding hookup culture?

“Finding someone who genuinely wants to spend a large amount of time with you”.


“Finding someone who wants to be seriously committed.”


“Finding a guy who is interested in getting to know you versus just wanting to bring you home.”


Is it managing expectations?

“Expectations: making sure yours aren’t too high or too low.”


Or is it, at this one 20-something put it:



When today’s 40-somethings look back on their 20’s, do they remember the same things as being hard about dating?


The 40-Something Perspective

By Christina Vuleta

I was surprised at the initial lack of response to this question. I wondered if it was a case of dating amnesia. The memories are less specific but reflect some of the same issues!


I got two responses of only good times  — “I had the time of my life dating in my 20s.”  One of these responses was from a woman who spent half of her twenties in a committed relationship and the other half catching up. She recalls not having trouble getting dates but feeling like she was way behind on what the rules were. How long do you wait before you call? Why didn’t he call? When do you sleep together?


Back then it was the era of the rules – both the “three date rule” and the loved / hated book of the same name. The Rules was original published in 1995 when many 40-somethings today were getting to their prime “Maybe should I think about getting married” days and suddenly searching for the one. Dating was not a sure way there.


Men are accused of perpetual adolescence today but the man-boys existed back then as well. Meeting men that were ready to commit was hard for some.


“I was used to dating in high school – that was what you did. Then you get to college and post-college and no one dated. They just hooked up. You couldn’t get a commitment. What I thought dating was didn’t exist. Even after graduation it was just like college with money. No one wanted the responsibility of dating.” – 40-something, lived in Chicago in 20s, now in NYC.


Indeed it was the lack of control that got most women unhinged. When probed even those that loved dating fessed up to not liking the games or the waiting for the call.  We didn’t have texting or sexting back then. It was much harder to find a crush that’s for sure! And there were no online options to cut through the clutter. That’s not to say women didn’t also do the calling — but it was much harder than sending a text where you didn’t have to hear the awkward pause.


A few found it was the guys timeline that made dating hard. One 40-something woman shared her dislike that as entered her later twenties it felt like every date was a try out. The guys she found herself with were auditioning wives while she was still jones-ing for some freestyle romance. It was a case of the guy looking for the girl who looks right on paper. The downside of this scenario was that it pricked her insecurities and fears. Did she dress well enough?  Was she intelligent enough? Was she  pretty enough?


Looking back, this is what many women “wish they knew then”.  Why did they try to be someone else to be attractive to a potential date or let that person make them feel bad about who they were?

“In my twenties dating was all about could I live up to the date. I was already a pretty cool person. I was very evolved. I know that now but I didn’t then. You learn to appreciate how unique you are. We really don’t need more people fitting in. When you are authentic and happy you make a good partner. You can’t do that if you are worrying about impressing others.” – 40-something, wellness coach, NYC


On the other side there definitely was a contingency that didn’t take the rules too seriously. Dating was too “old-school” or just plan old.

“I didn’t like dating. We all thought it was weird if someone asked us out for a date! That was so 50 years old”. – 40-something, Boston.


“We didn’t date. Despite the fact that there seems to be the sentiment that ALL OF A SUDDEN people don’t go on dates anymore, I feel that this is more of a 20-something thing rather than a “new” thing. When I was in my 20’s I thought dates were goofy! Just wasn’t happening. We moved in groups, hooked up and if we did happen to establish ourselves as a couple it really didn’t change the group dynamic. Even if I met someone that wasn’t in the group they definitely had to fit in or it wouldn’t work.


I didn’t go on real ‘dates’ until I was in my 30’s! And I must say they both have pros and cons. I often missed the organic and natural way that things happened in my 20s. If two people really liked each other they spent more time together and it gradually turned into something. Dates are always fraught with so much pressure…”Is it too soon for (fill in your favorite)?”


On the other hand dating gives you more control because it’s more defined as to why you’re there without the 20-something questions like, “Are we just friends?” Or “are we just hooking up?” I haven’t dated in my 40s but from what I hear there is a little less pressure than the 30s because a lot of women are past the marriage/baby track and just want to have fun again and meet a partner. – 40-something, New York City


Net net:  I would say the dating hardships are not all that different.  I love this quote from Ann Sheybani, a 40:20 Vision contributor and wisdom sharer who blogs about life and relationships at Starting Over.  Be patient and be yourself!


“The right man will move heaven and earth to be with you–the real, authentic you with all your wonderful flaws.” – Ann Sheybani


P.S. And stop waiting for the text and start getting into what you love doing.

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