18 Differences Between Dating A 20-Something Versus A 30-Something

18 Differences Between Dating A 20-Something Versus A 30-Something


Dating means something quite different when you’re in your teens, your twenties and your thirties.

The amount of life experience at each decade is incomparable, which is why dating someone much older or younger than you can, sometimes, be difficult..

This isn’t to say that it isn’t worth it, but it’s just another challenge in the already difficult dating world. Your friends are at a completely different part of life than his friends, which is probably one of the leading factors of what makes this so difficult.

So, what are the biggest differences of dating 20-somethings versus 30-somethings?

1. Your 20-something boyfriend is concerned about the pregame, your 30-something boyfriend is worried about a babysitter.

It’s funny, yet eye-opening, when one’s biggest concern is which one of his friends’ houses he’ll be pregaming at while the other’s is looking for people to watch his kids.

You may be laughing at the situation, but you can bet he isn’t.

2. Your 20-something boyfriend does date night during the week; your 30-something boyfriend prefers the weekend.

A 20-something never wants to give up a weekend night for a simple date. I mean, those nights are reserved for friends; the weeknight is when you’d prefer to go out to dinner or drinks.

But when you reach a certain age and are over the party scene and work incredibly long hours, the weekend is the only time you’d ever think of going out on a date.

3. Your 20-something boyfriend is deciding which bar to head to; your 30-something boyfriend is planning where he’ll having his wedding.

The most important destination in a 20-something’s mind is what bar he’ll be drinking at for the night.

The 30-something you’re dating? He’s just trying to pick a reasonable wedding venue.

4. Your 20-something boyfriend spends his Saturday mornings hungover; your 30-something boyfriend is doing errands.

A 20-something won’t even venture outside until it’s after 2 pm. The 30-something, on the other hand, has already hit the gym and gone food shopping.

5. Your 20-something boyfriend’s idea of a relaxing night is not blacking out; your 30-something boyfriend is not drinking.

A 20-something is still at that stage where going out means getting obliterated with friends. A 30-something hasn’t been into that for years — and thank God for that.

6. Your 20-something boyfriend shares an apartment; your 30-something boyfriend lives alone.

Chances are a 20-something can’t afford to live on his own so he’s forced to find roommates. A 30-something is financially stable and has been living the solo life of luxury since as far as he can remember.

7. Your 20-something boyfriend lives on Seamless; your 30-something boyfriend loves to cook.

A 20-something should probably know how to cook by now, but sadly Seamless seems to be the best option for him. A 30-something knows his way around the kitchen and isn’t afraid to spend ample time there.

8. Your 20-something boyfriend played around with Tinder; your 30-something boyfriend thought Tinder was the answer.

A 20-something isn’t overly concerned with finding someone and settling down. A 30-something has Tinder and every other dating app to ensure that he won’t end up alone.

9. Your 20-something boyfriend’s biggest concern has to do with tomorrow; your 30-something boyfriend is all about a 10-year plan.

A 20-something’s biggest concern is whether he’s going to make it in time for his haircut appointment. A 30-something? Taxes and a mortgage.

10. Your 20-something boyfriend can’t imagine deviating from his routines; your 30-something boyfriend can’t wait to integrate you in his.

It’s taken long enough for a 20-something to have a schedule, so there is absolutely no way he wants to rearrange that, not even for you. A 30-something, on the other hand? He can’t wait for a new way of life that most definitely includes you.

11. Your 20-something boyfriend dreads meeting the parents; your 30-something boyfriend can’t wait.

A 20-something doesn’t even want to go home, let alone bring a stranger for everyone to meet. A 30-something can’t wait to bring you home to meet his family.

12. Your 20-somethings can barely afford a train ticket home; your 30-something boyfriend has the luxury of a car.

Your 20-something boyfriend can’t even afford rent, let alone transportation; your 30-something boyfriend travels in style.

13. Your 20-something boyfriend already spent his Christmas bonus; your 30-something boyfriend invests his.

Your 20-something boyfriend can’t wait to blow his bonus check on shots at the bar and a Christmas present for his mom; your 30-something boyfriend has already deposited it and is spending his interest on jewelry for you.

14. Your 20-something boyfriend doesn’t know what a budget is; your 30-something boyfriend knows how to balance a checkbook.

That 20-something boyfriend of yours checks his account balance on his blue Chase debit card on a somewhat daily basis. The 30-year old on the other hand, can balance his spendings in his head.

15. Your 20-something boyfriend still can’t pace himself; your 30-something boyfriend isn’t even concerned.

Pacing is not even an issue when you hit your thirties since you spent your twenties perfecting that. This is a major difference when going out with either men of different ages.

16. Your 20-something boyfriend still waits for the “exclusive talk”; your 30-something boyfriend is solely dating you.

Well, that’s just awkward…

17. Your 20-something boyfriend still goes out all week long; your 30-something boyfriend rarely even considers that.

This probably has something to do with their respective maturity levels — and also that hangovers do not age well.

18. Your 20-something boyfriend is the only taken on in his group of friends; your 30-something boyfriend is the only one left to get married.

Let the pressure begin!

Ashley Fern


#Relationships  #30somethingBoyfriend  #Tinder  #Seamless

Published by

Robert Chaen

Global CEO-Founder of ChangeU and Movsha Movers & Shakers, Hero-CEO Whisperer, Writer, The #1 Alpha Change Expert, Father of Asian FireWalking Robert Chaen is an International Keynote Speaker, writer, researcher, and corp games designer. He is famously known to be the “Hero-CEO Whisperer”, 1-on1 coaching with many CEOs and Celebrities for corporate strategies, staff & office political issues, personal branding, and even public figure OSHA safety drilling called Drager Defense. He has transformed CEOs and managers in Coca-Cola China, TVB Hong Kong, Cathay Pacific, Hong Kong Airport Services, VADS, TM, Public Bank, Auditor General's Office Maldives, etc. He is the prolific creator and online Author of innovative management tools such as DragonCEO, Diamond Leader, Papillon Personal Effectiveness, OSHA Drager Defense, KPI Bank, etc. He is also the Founder of Movsha, an international networking with monthly mingles with MOVers & SHAkers, Angels, Entrepreneurs, CEOs, Celebrities, HR-PR-CSR, HODs, and the Most Influential IDEA people. ​Chaen is widely considered as one of the top International Platform Keynote Speakers for Resorts World Genting Senior Management Conference (Manila), 7-Eleven HK, Samsung, Coca-Cola China Mini-MBA @Tsing Hua University, Cathay Pacific, Hong Kong Jockey Club, The Story Conference where he interviewed Datuk Kamarudin (Chairman of AirAsia) and Siti Nurhaliza. He has been widely featured in TVB, AWSJ, CNBC, SCMP, The Star, and Sin Chew. As “The Father of Asian FireWalking”, he coached TVB celebrities (Ekin Cheng Yee-Kin) to walk on 650°C fire; and raised HK$68M in the world’s 1st and only live TV Charity FireWalk (TVB Tung Wah Charity Show), before Tony Robbins even came to Asia. If Robert can get you to walk on 650⁰C fire, he can inspire you to be THE BEST. He champions CN-HK-EU-US Tycoons to be philanthropic, and to be angel investors to support the next generation of Jack Mas, Steve Jobs, Richard Bransons, Steven Spielbergs, or Barrack Obamas. With some slick motivational speakers with fake doctorates out there, graduates often describe Robert to be "the most credible, empowering, truthful Coach" who believe in his graduates to believe in themselves. ​However, clients have described Robert as "The #1 Cool Badass Alpha Change Expert". He has the coolest first class stature, rapport and trust from clients. He will not hesitate to tell the badass truth ever so gently because clients are paying him big bucks to reveal the truth, find solutions, persuade the hostile HODs, and align cross-teams within the organization. Originally based in Hong Kong for 20+ years, he had worked with top Branding/Ad agencies at J Walter Thompson and Leo Burnett, and was a certified FranklinCovey (7 Habits) in USA, and NLP MasterCoach (USA). His warmth is known to soften the most hardened, resistant sceptics. He will inspire your team to Go for Top 1, or to be a Dragon CEO. With boundless energies, Robert owns 15+ successful business Joint-Ventures, and created unique products under his global VC network called Chaen's Angels VC. He is deeply passionate about ChangeUTH Youth CSR, Science-Based Medicine (vs. quackery), short films and Reality TV. Touched by a personal tragedy through the loss of his HK-born Portuguese wife, co-coach and business partner, Brenda José of 18 years, Robert explores the many ways in which the spirit world is communicating with the living with real scientific studies and evidence. He gives inspiring conferences on The Secret Afterlife.

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