8 Immature Behaviors That Will Keep You Painfully Single If You Don't Outgrow Them

Still stuck in the dating cycle? Thee habits might be the reason love keeps slipping through your fingers.

Last updated on Jun 17, 2025

Painfully single woman, who has immature behaviors. Giulio Fornasar | Canva
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As we grow, advance, and (hopefully) mature as adults, the ways we live our lives should progress at an equal pace. What I find to be an epidemic these days is that otherwise seemingly mature and well-adjusted men have stuck to the dating habits they learned in their early 20s, or maybe even late teens.

Back in those days (listen to me, sounding like an adult now that I've turned 30), a lot of different things accomplished a lot of different goals. Maybe you didn't want a serious relationship. Maybe you hadn't figured out yourself or what you were looking for.

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But now that you've matured past that phase in your life, you cannot expect to get better results by utilizing the same old techniques. If you're going to find yourself a nice girl who you'd feel comfortable bringing home to mom, there are some strategies you're going to have to leave behind — because they just don't cut it anymore.

Here are eight immature behaviors that will keep you painfully single if you don't outgrow them:

1. Using the 'let's just see where this goes' technique

woman with the immature behavior of let's see where it goes technique Perfect Wave / Shutterstock

As you reach your 30s, and definitely after you hit them, women are past the point of wasting their time with guys who aren't serious about a future. Women are driven, successful, and independent, and want to be with a man who they can consider an equal teammate in life and love.

The whole "I'm still figuring life out" thing isn't going to cut it with a mature, established woman. Trust me, I know better than anyone that life is tough and a lot of us probably have no idea what we're doing.

It's not about having all of the answers — because nobody does — but it's about having some semblance of a path in life that will make her feel comfortable committing to you for the long run. Nobody wants to plan a future with someone who doesn't have a future planned for themselves.

RELATED: 10 Biggest Mistakes Women Make When Looking For Love

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2. Waiting three days to call someone you're into

woman with the immature behavior of waiting days to call fizkes / Shutterstock

Traditional antiquated dating "rules" go out the window when a certain level of maturity is reached. Call when you want to call, text when you want to text. There are no rules or regulations when building a mature, healthy relationship.

If you start overthinking everything and only doing what you think you're supposed to do (or not do), the genuineness of your actions begins to fade and give way to a more robotic structure in your relationship. How can someone get to know the real you if you're manufacturing every step you take? Oh, they can't.

The three-day rule might have been a way to create intrigue in the past, but modern dating values authenticity and timely communication. A 2022 study explained that the disadvantages of this rule involve increased anxiety, misinterpretation, disruption of momentum, inauthenticity, self-doubt, and unrealistic expectations. Building genuine connections and communicating openly are considered more effective approaches.

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3. Sending a 'Hey, wanna meet up?' text

man with the immature behavior of hey wanna meet up texts Gorodenkoff / Shutterstock

I've mentioned this one a few times before because it's an ongoing issue. If you want a woman to take you seriously, you need to let her know that you're taking getting to know her seriously.

A last-minute text to see if she wants to "meet up" somewhere you're going to be, isn't exactly sending the message that you're willing to put in effort for her.

Meeting up for a drink isn't a date. Grabbing a coffee isn't a date. A last-minute text inviting her to join you out with your group of friends isn't a date. Using the actual word and properly inviting a woman on a date is the first step to actually making it one.

The next step is taking the time to plan something out. Stand out from the crowd by showing her you're different than all the other guys — because you are.

Research strongly suggests that excessive or inappropriate phone use on a date can lead to feelings of neglect and exclusion, hinder communication quality, decrease relationship satisfaction, and potentially increase conflict and jealousy. Being mindful of phone use and prioritizing face-to-face interaction is crucial for fostering healthy and fulfilling relationships.

RELATED: The Honest Reason You're Still Single, According To Your Personality Type

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4. Scrolling on your phone during a date

man with immature behavior of using phone on date Alisha Vasudev / Shutterstock

Honestly, this is so cringeworthy that I hate to even need to bring it up. Maybe when you're younger, you can both play around on the Instagram machine while you're waiting for your fries and chocolate shake to be roller-skated over to the car. But you're an adult now, and it's time to control your impulsive urges to check social media every 5 seconds.

I know that you're important and you need to see who just liked your profile photo, but when you're on a date with a real-live person who is deserving of your attention, that's precisely what you should be giving her. Have a real conversation, give her your full attention, and leave your phone in your pocket.

RELATED: 5 Odd Behaviors Of Pretty Women Who Never Get Asked Out

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5. Wasting time on people you're not into

woman with the immature behavior of wasting time on people not into New Africa / Shutterstock

I think we've all probably spent a little too much time with someone who we knew, deep in our hearts, wasn't right for us. The reasons could vary.

Maybe you'd feel too guilty breaking it off with them. Maybe you thought you'd develop stronger feelings for them eventually. Maybe the intimacy was great, but nothing else really was.

When you're younger and not looking to plan a future, it may be nice to be with someone just for companionship, as long as you both are looking for the same thing. But when we get older, it's time to get a little more serious about who we spend our valuable time with.

If you know in your heart it's not going to work in the long run, break it off for both of your sakes. Nobody should be led into a dead end.

RELATED: The Way We Date And Marry Is About To Change — 8 Trends To Watch, According To Research

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6. Not being genuine about who you are

woman with the immature behavior of not being genuine OWL_VISION_STUDIO / Shutterstock

Too many people send their "representative" on the first few days with someone new. You're on your best behavior, you're polite, courteous, patient, and chivalrous ...

While you should absolutely be all of these things, you should really, truly, genuinely be all of these things. If you're not, don't pretend that you are, because when the truth comes out, it's just going to make things worse.

If you don't possess these qualities, work on yourself first and develop them before you enter into a relationship with another person. "Fake it 'til you make it" doesn't apply when someone's feelings are on the line.

Research suggests that while it may be tempting to present an idealized version of yourself when dating, prioritizing authenticity is a more effective strategy for finding genuine connections and building successful, fulfilling relationships in the long run. When partners are genuine, they are more likely to understand and respect each other's true selves.

RELATED: If You’re Single And Fed Up With Modern Dating, You Need To Hear This

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7. Putting no effort into how you present yourself

man with the immature behavior of putting on lame going out outfit New Africa / Shutterstock

Guys, the cargo shorts and Polo shirts are great for casual days with your friends, but if you're taking a woman out on the town, you're going to need to step it up. First impressions are important, and unless she's looking for a frat boy, you're probably not going to want to look like one.

RELATED: 13 Mistakes Grown Men Don't Realize They Make That Annoy The Women They Love

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8. Letting her pay half

man with the immature behavior of letting woman pay Srdjan Randjelovic / Shutterstock

When friends go out, they split the bill. When you're on a date, the man picks up the tab. All of it. There are plenty of ways a woman can reciprocate if she'd like: she can take care of parking, pick up a round of drinks, get the snacks at the show you got tickets for, whatever it may be.

But when the tab comes for dinner, don't let her anywhere near it (and don't accept her offer to split it). If you think paying for the date is about the money, think again. Of course, dating changes as we get older.

While splitting the bill equally can be a positive step towards financial equity in a relationship, it's important to acknowledge the complexities involved. A study by Chapman University explained that traditional gender roles and expectations still influence perceptions of dating etiquette, which can lead to unintended consequences and create discomfort for both men and women.

Life is all about progressing and evolving, but it doesn't happen automatically. Things change on their own — we all know that happens without us needing to put in any effort. But improvement? That takes work.

Work, though, is what makes the final result so rewarding: A happy, healthy relationship with a woman you love.

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James Michael Sama is an internationally recognized speaker, author, and relationship coach. He is a go-to expert with outlets such as CNN, Bravo, The New York Post, The Huffington Post, The Daily Beast, CNBC, The Boston Globe, CBS, and more.

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