Dating 20s vs 30s: A guy's perspective

30-something man explains his views on dating after his 20s. 

What you are about to read is an analysis from a 30-something single guy on dating in your 20s vs 30s.

Dating ain’t easy, no matter how much fun it can be, or not be.

   “To be, or not to be” is the question that Shakespeare’s Hamlet asked of himself about life; which only now as a man in my mid-to-late-thirties is better referenced in the dating world.. 

  

To be single, or not to be single.  To go on “this” date, or not go on that date.  To make a second date happen, or to not make a second date happen.  To be the single man in your neighborhood, your workplace, your house of worship, your circle of friends that let you be you, that support you, or are weary of you, those that feel sorry for you, (from their own perspective) and those that are jealous of you because they still see the blue war paint as you stand as a symbol of their own long-lost days of independence while in their mind you scream “Freedom!” in the relationship version of Braveheart, yet in your opinion it sometimes can be more of a lonely heart.

But, however one might look at the single life, dating is either for temporary companionship, if nothing else to get to know a new person that either leads to never seeing them again, to a friendship, or it is for something more serious which evolves into a relationship and marriage. 

   Dating ain’t easy. 

   

A perpetual job interview search that continues on until you land that perfect “job” as someone's boyfriend or girlfriend, then promoted to fiancé and finally the big chair itself:  Spouse.

Why do I keep saying dating ain’t easy? If you think it is then you’re not doing it right.  

Meeting someone, going on a date, putting yourself out there (other than socially) and then never hearing from them again – if you go on a lot of dates with a lot of different people, and you really enjoy it – you’re not doing it right. 

Don’t get me wrong… dating is enjoyable, but like anything else there is an effort that must be applied if your serious about dating. As a man in my thirties I feel more confident of whom I am now than I did in my twenties, I know myself, I know what I want, I know where I’ve been, I’ve learned a lot of valuable lessons through my own trials and errors and from observing others, but I’m also more tired.  No, I’m not “old” tired – I’m wise tired.  Big difference.

Wise tired, whether you feel like you keep making the same mistakes, or have learned from them is a "tired" of constantly realizing you haven’t found the right person – and let me stop you here and say if you date and have no care or concern about ever taking it serious and finding the “one” then stop reading now, because you’ve already wasted a lot of your time as it is and I don’t need people like you trying to understand or relate; or comment or have your opinion because if you can’t take the math problem serious then don’t even attempt to solve the problem.  You won’t care and you won’t get the correct answer – you just are lonely and have nothing better to do, I guess.

   
To the rest of you: Why are you still single?

Hopefully it’s because you didn’t compromise and “settle” so you haven’t given up, and if you did “settle” then that’s probably why you’re back in the dating world again because it didn’t work out and you want to do it right this time. 

Sometimes in your dating life, you juggle. 

   Thirties dating isn’t twenties dating – Let’s get that said right now before I go any further. 

   

Men dating younger women, women dating younger men: you’re actually hurting yourself more than you are the 25 year olds you like going out with… it isn’t the same – it isn’t the same – it isn’t the same as if you were the same age as your twenty-something year old date.  Quit it. Quit it now and stick to your decade. 

Or…. Ignore me and then read this again next year when the relationship falls apart.  It’s your choice. 

   
Dating in my thirties is much different than when I was twenty-something.

Yes, there’s still restaurants.  There’s still movies to go see, and conversations to have, but you’re 37.

What?

   

Okay, you’re 33 – whichever - A duck is duck no matter if that duck is 33 or 37, but a twenty year old is whole different story. As a single straight man growing up during the time I did, my generation saw more change than any other one that has ever existed on this planet.  How? 

   

When we were born we had basic antenna TV and some of our parents still had rotary phones – up to a point, even if you were too young to remember them being replaced with touch-tone phones.We graduated within a few years of the millennium – either late 90’s or early 2000’s and we went from basic cable tv, to email and internet being introduced in our teenage years, to one day waking up to Facebook, YouTube, snapchat, smart phones, GPS on our phones, instant everything right now, yet when we were kids our parents didn’t have a clue where we were if we didn’t leave a note in the kitchen and had no way of contacting us unless they knew where we were and could either drive there, call there, or send the police.

   
Now – instant text. Instant call. Instant videos. Instant everything.There’s even “instant” dating for those of you whom have tried online dating – meet a girl on your phone on Tuesday and you’re out to dinner with her by Friday.Has the “instant text” manipulated us into expecting unrealistic dating expectations?  Or have we got to the point in our lives when we “aren’t as young as we used to be” and a small spark of panic – however unnoticeable – flickers in our minds and we realize that we’re closer to 40 than we are 30 (if not already) and it’s time to find the “one.”

   
No other generation after us will go through what we’ve experienced.  They’ll know no different. They will experience the change of dating at a different maturity level, but never the technological advancements that followed us through our lives from 17 to 37.

But let’s stick to the “mood’ and the “feelings” of dating in your thirties compared to your twenties:

   
Personally, and criticize me if you wish – everybody is an “expert” these days, - I believe men, just like women, are in an unspoken hurry to find a mate to grow old with. In my twenties the boys wanted to play and the girls wanted to get married – and then some did and some didn’t, but some of the ones that did got divorced later, and now they’re at it again – looking to not make the same mistakes they did last time – which immediately a woman will rule out possible men that she wouldn’t have ruled out 10 years earlier.

Most, but not all, have kids.  I don’t.  I’m still a single, childless thirty-something year old man. Some women see that as a red flag: playboy, self-focused, asshole, immature, uncaring about others. Other women see that as the perfect man: No baby momma drama, no ex-wife, no kids (we can have kids or he can help me focus on mine), he knows what he wants, he works hard, he should be financially stable since he doesn’t have a family he’s been paying for the last decade..

  
How I see it: Engaged, not engaged, engaged, not engaged, very picky about my dating because I know what I want, losses and bad experiences put off dating for a while, work a lot, seen too many friends get divorced so I am not, not, not going to settle… I know what I want, I know whom I am, I know I deserve better and she deserves my best I can give her – where is she?

Which leads us to our next part: 

   
If you’re a twenty-ish year old girl posting sexy selfies all day long that’s your business – men  (excuse me, boys) aren’t dating you for commitment anyways – and if they are wanting commitment they’ll learn they can’t tie you down – and women at that age that want commitment want it from the rebels, the black sheep, the troublemaker, because he’s exciting and you think it’ll make life more exciting and you can do this whole “let’s grow old together” thing because it’ll be exciting!

   
Ladies in their 30’s are laughing and shaking their heads right now – because they know better. They want a man. They want a man who has his shit together and just doesn’t PRETEND to have his shit together.

   
A man wants (my opinion) a woman whom is focused on building a serious relationship (but not too quickly) whom can be an excellent partner, a wonderful mother, serious about life, but likes to have fun with you there- not an attention seeker from other men, but not an introvert afraid to speak her mind and be herself, someone friendly and happy about life.  A man also wants a woman who has her shit together – and yes we can say shit – we’re adults, if that’s too much for you then you can’t accept reality and refuse to compromise and that’s a red flag.

Silhouette of a tired man. 

 But back to being tired - I’m tired.   I am.  

  
I don’t need Betty Crocker or Barbie, but I do need someone willing to go hand-in-hand through the rest of this journey together that isn’t 25, but doesn’t act 65 (yet) whom knows who she is and what she wants and not that “I’m 25 and know what I want right now” crap, but honestly can tell me what she wants and hopes for, her dreams and desires, and expects me to step up to the plate and hit a home run, but doesn’t try to coach me, because she knows that I got this.  

  
Fast Food is for twenty-ish dating; the French restaurant is for us thirty-somethings – we appreciate a good thing and know how to enjoy it, but when I get home my necktie is coming off and your dress better know how to find its way to the floor, because I have some serious work I’m about to do – this ain’t playing – I’m in it for life!