As a millennial, it’s safe to say that today’s dating culture is very.. um interesting and it can be hard (and disappointing) to date in your 20s.
Dating today feels like you’re in a giant lackluster pool of hurt people hurting people. Nobody seems to value honesty or remember how to communicate and with so many options people can’t make up their minds.
All the dating horror stories that exist between myself, my friends, millennial’s on the internet and in the rest of the world doesn’t make it sound too promising.
Is there any hope for millennials and all the ones after? Somebody pray for us!
Personally I go through phases of being open to going on dates and then being off for a season because honestly dating feels like you’re doing quantum physics in your head sometimes.
Last year, I had a wild idea to go on 50 dates in 1 month to see what I could learn. Try not to be shocked but I had to tap out after 4, because it sounded waaay more fun in theory.
Since reading, The Defining Decade by Meg Jay, it really reiterated to me just how important it is to plan and to choose a future partner based on the kind of family and future you want to build for your life versus just on how someone makes you feel.
Dating is quite an interesting subject to me because everything comes back to psychology and sociology.
I’ve done quite a bit of research through personal experiences, books, YouTube videos, podcasts and hearing other peoples stories and have juiced out all the important dating tips.
While I’m not a dating expert by any means, I do think that I give great advice even if I sometimes can’t take it myself.
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Tips for Dating in Your 20’s
Make a list of what you’re looking for in a partner
We make lists for our groceries so why not make a list bullet pointing the kind of person we would potentially want to spend the rest of our lives with?
When you’re young, you have time to spare dating people who probably aren’t the best for you (and that your parents hate), but once you get older you should hopefully be more realistic.
A good list should include the things you must have in a partner, things you’re willing to negotiate on and things that are deal breakers for you. You can start by writing 10 for each category, then narrowing each down to top 5 and then to top 3.
It’s key to not be delusional because no one is going to have everything on your list and if you think you will, you will probably be single for a while.
I’m constantly refining mine, but a few things my list includes are really sweet, positive outlook on life, and funny for must haves. Not in a creative field and being short as some of my negotiators. Then cigarette smoker, inconsistent, and no drive or passion as deal breakers.
By having a list, you’ve got a clear vision of what you’re looking for and have a nice little standard set for yourself.
Choose which is more important to you: Compatibility or Chemistry?
As you start dating and building a roster (more details later), you’ll see the different ways that you can connect with potential partners and what means more to you.
One person you might enjoy because you have the same interests and values but it’s a slow burn and another because you feel like fireworks whenever you’re together but have a lot of differences.
So which one do you choose?
I wish the answer was easy but it’s not so it helps to know which is more important and sustainable for you.
Be confident and comfortable with yourself
Honestly the only way to actually have fun while dating is to be confident in what you’re bringing to the table so if someone isn’t interested in you, you’re not even bothered.
People can tell when you’re insecure and it’s too early to be showing your weaknesses when you’re getting to know potential partners.
Never forget that people are humans first and you never know peoples’ true intentions. Opportunists are out there and meeting the wrong one might start a whole lot of mess for you if you’re vulnerable too early.
Remember that you show people how to treat you
In hindsight, I realize how easy it is to put the blame on someone else for their lack of effort in the courting phase.
But realistically, how can you be mad at someone for not doing something you never asked them to do?
In the beginning is when you should set the tone for what you will and will not accept.
If you’re not okay with constant last minute canceled plans, childish behavior or playing Houdini then let it be known ASAP and if after that they still don’t respect you then be quick to cut them off.
Be the one who cares the least
I should preface by saying that when I say “the person who cares the least”, I mean the person who isn’t taking things too seriously, just living your life and having fun.
Unfortunately, dating can be a game and if you’re gonna play, the person who cares the least is the one who has the upper hand.
It can be easy to get worked up when someone cancels plans, takes hours to respond, or is inconsistent but if you’re just out here doing your own thang then you won’t even sweat.
Be open minded to different types of people
A good way to approach dating is to look at it as a funnel. Everyone knows how a funnel works so obviously the top is the biggest opening with the narrowest part at the bottom.
When you first start dating you should be open to receiving interest from people who may not technically be your “type”. Then as you get to know people, your pool gets smaller and smaller until you’ve got the one who you know deserves to make it to the end of your funnel.
If you go into dating bee lining for a chupacabra then you might be buzzing around for a long time.
Have no expectations when meeting people for the first time
One of the worst things you could probably do before meeting a potential partner for the first time is to have all these expectations of how you think they’re going to be or how you want them to be.
Five year deep social media stalking might as well be self sabotage because you’re naturally going to make assumptions which could make it hard to not have expectations. And depending on what you find, those premature details may be hard to forget later.
In addition, I feel like there’s less pressure because you don’t subconsciously feel the need to try and act like the kind of person you think they would like based on what you assumed.
What I like to do is go into it not even looking at it as a “date”. In that present moment, that person is a stranger who might become a friend so why should I think about it too much?
Minimize texting too much before meeting for the first time
This one goes along with the same idea as above because depending on how long you text back and forth before meeting this could create a false world that might not translate into reality.
I made that mistake once before going on a date with a guy I matched with from good old trusty Tinder. He was totally my type face wise and when we messaged back and forth there was good cheeky banta (que Australian accent).
When we met I had never been bamboozled more in my life. He gave off the energy that there was nothing exciting going on in his life which quickly masked any kind of physical attractiveness.
I was definitely way more optimistic than I should have been so needless to say, we never saw each other again.
Get drinks over dinner for a first date
As a first date, I would definitely prefer getting drinks over dinner for multiple reasons and I barely even drink alcohol.
When you sit down for a meal on a first date, it gives your date an end time versus if you go get drinks. With drinks, you can just sit at the bar for x amount of hours and easily lead the date into more activities after a few drinks.
Overall, I feel like getting drinks on a first date makes you feel more free and laid back because you don’t have a waiter constantly interrupting, don’t have to eat and talk at the same time.
Plus and most importantly, it’s easier to leave a bad date after one drink versus feeling awkward and waiting for a whole meal to be over.
Playing the Game
Build a roster by dating multiple at once
One of the smartest things you can do to not get attached to a single person when dating is to build a roster of potentials.
It’s game time and you’re the coach, because you’ve got your starters on the field, a few on the bench and others waiting to be drafted.
Back in college, my roommates and I used to have so much fun attempting to build a semester roster. You know for a fact that guys do it, so why can’t women?
Dating (not sleeping) with multiple people at once makes it easier to stay level headed. Building a roster is key to not get prematurely attached to anyone and it helps you truly see the kind of person you’d want to be with.
In theory, a roster sounds bad ass, but personally I think that a roster is hard to keep track so I can never keep it going longer than a month or two.
When you’re getting to know multiple people at once, it’s quite easy to forget who told you what and personally, I always end up liking one person more than the rest and ditching the others instead of keeping them all steady.
Broaden your age range
Sometimes you lose hope in the boys of your own generation so you have to dip your toes in another.
As they say, age is just a number and there’s even a niche on YouTube for age gap relationships.
I think it really comes down to what you’re looking for but personally I wouldn’t want to be with someone 10-15+ years older than me. That’s too many years of someone being able to do shit that I don’t know about. Plus that’s so much past life to catch up on.
Depending on the how large the gap, someone could have legit lived a completely different life with a different name all before meeting you.
The two oldest guys I ever went out with was 42 and 38 and yeaah it’s a no from me dawg. One of the longest relationships one of the guys said he’d been in was 16 years and they were never engaged.
I don’t know about you but I heard and saw loud red sirens going off after that.
Personally, I think there’s more fun being in the same life phase as your partner. People of a particular age have put in the work, lived their lives, and are just ready to chill.
Having feelings for someone doesn’t mean you should be monogamous
This was probably one of my biggest down falls when it came to dating.
It’s so easy for me to see potential but I never really understood just how much work it takes to love and sometimes love isn’t always enough.
I recently read a book called The Art of Loving by Erich Fromm and it was such an easy and insightful read.
A good part that relates says, “love, experienced thus, is a constant challenge; it is not a resting place, but a moving, growing, working together; even whether there is harmony or conflict, joy or sadness.”
Feelings are natural and if you allow yourself to feel them you’re going to be gravitated to what makes you feel good.
But you have to remember that what makes you feel good, isn’t always good for you.
Go on dates consistently
I’ve heard that dating is a numbers game. The more dates you go on, the higher chance of meeting your future partner?
Not sure if it’s true but I do think that by constantly going on dates you can refine what you’re truly looking for, get to know more about yourself and others, and just get better at dating overall.
Other people are our biggest teachers so even if a date doesn’t lead to anything more, there’s always a lesson to learn.
Also, you never really know what might come of meeting someone new. Let’s say you mutually decided to just be friends with a person you go on a date with and then they invite you to a party where you end up meeting your “perfect” person.
Put yourself in positions to meet people
It’s usually the people who stay at home every weekend that complain about how all the good people are taken.
Sadly, your special someone isn’t just going to knock at your door so it’s up to you to make yourself available and in positions to be seen.
If you live in a big city or close to one, there’s definitely a ton of events going on all the time filled with lots of single people.
It’s so true that you could literally meet the person of your dreams anytime and anywhere so it never hurts to always be on your A game.
Take people for who they are
The most applicable quote for this is, “when people show you who they are, believe them” by Maya Angelou. I feel like if everyone followed this while dating then they could save themselves so much headache.
It’s crazy how easy it can be to overlook less than pleasant traits when you see potential. If someone tells you that they see red when they get mad, have cheated before, or that they have a hard time keeping friends, you better re-evaluate sis.
As we get older, it’s more likely that people are stuck in their ways making it a lot harder to try and influence someone for the better so it’s best to just let people be.
Only have casual sex with people you don’t like
This one is a toss up for me because I believe every situation is different and what works for you might not work for someone else.
There’s an exception to every rule and I’ve heard quite a few stories of people hooking up on the first night and still being together years later.
I’ve heard a good rule of thumb is to only have casual sex with the people you don’t actually see a future with and it definitely makes sense.
When you’re trying to build a forever bond with someone you want to have a strong mental foundation, build the excitement, and be clear headed on where things are going.
Sometimes being intimate too soon can make you feel like you’ve got a never ending fog machine going off in your head and that’s never fun.
Some people have the magical gift of being able to separate sex and emotions, but for others it might be easier to not get them both confused when you only have casual sex with people you wouldn’t be monogamous with but to each their own.
Lastly and most importantly is to just live your life the way that makes you feel happy and the most fulfilled.
If you don’t see a partnership in your future then you shouldn’t waste time trying to feel something that you don’t. And if a fairy tale ending is all that you’ve been dreaming about since you were five, then go out there and find your prince or princess.
The constant advice that I’ve gotten from older people regarding relationships and marriage is to stay single and never get married so *shrugs shoulders* looks like we’re all fucked.
Do you have any dating tips to share? Let me know in the comments.
Thanks for reading and stay hungry to learn, create and grow!