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Pros And Cons of Dating A High Maintenance Woman

By Emyli LovzOctober 5, 2019Strategy
dating a high maintenance woman

Are you considering dating a high maintenance woman?

High maintenance is synonymous with needy, egocentric, and preppy. It’s generally not a label that one likes to flaunt around. Your friends would all tell you to steer clear of a high maintenance woman. Let’s be honest, you’ve rarely if ever have heard anyone speak highly of a woman that’s high maintenance. I know this might ruffle some feathers, but it’s time to go against the grain. There are in fact some pros that come with dating a high maintenance woman.

For the longest time the female high maintenance archetype was Paris Hilton. She’s obsessed with high fashion, is a bit vapid, and fetishizes pricey brands. But to be fair, even Paris Hilton must have some redeeming qualities. The media has turned her into a caricature. When we slap the label of high maintenance on someone they’re immediately associated with all the negative qualities Paris Hilton possesses. So let’s make this an exercise in dropping our prejudices and reevaluate the pros and cons of dating a high maintenance women


Pro #1 of Dating a High Maintenance Woman: She’ll Make You Look Good

Let’s go ahead and count the ways in which she’ll make you look like a boss. 

1) You don’t really think a high maintenance chick is going to date a gauche man do you? Her fashion will rub off on you one way or another. Either she’ll actively freshen your style up or you’ll feel awkward going out with a fashionista while looking like a frat bro. 

2) There were once those days when you walked into a room and no one noticed. Now, you’ve got a beautiful woman dressed to impress on your arm. You and her are going to turn plenty of heads. Are you ready for the newfound attention?

3) Your social media game is going to pop off. Not that getting more likes is a valid reason to date someone. That being said, becoming a minor influencer might just be a byproduct of dating a classy woman.

4) The halo effect is a real thing. If your co-workers and buddies see that you’re with a well-spoken, classy, well-dressed woman, your stock will rise. They’ll think of you as smarter, better looking, wealthier, etc. simply because you’re associated with this woman.

Pro #2: Daily Carnal Boost

Have you ever noticed that when people go on vacation they tend to dress up a bit more than they normally would? I call this the ‘vaca Insta’ effect. It’s when people dress up a bit more because they want to show off how amazing their vacations are. Imagine if your new girlfriend dressed this way every single day.

Dude, dressing up is sexy. Compare this new woman to your ex. The one that wore sweatpants all the time and rarely did her hair. How much more attracted do you think you’ll be to your new woman simply because she puts a bit more effort into her appearance? 

High maintenance women are sexy. They generally ooze confidence and pride themselves on their appearance. If that doesn’t convince you to start exercising in the sack a bit more I don’t know what will. Mid-afternoon sex is making a comeback!


Pro #3: She’ll Likely Push You To Greatness

HM women lust for opulence. They yearn for a 3-story house with a pool and flamboyant dresses. Fine dining isn’t a once in a while activity, it’s an every other week event at the very least. These women aren’t necessarily bratty or entitled, rather they want the very best. They won’t settle for not getting what they want. If you’re slacking professionally, socially, or emotionally they’ll ditch you.

Like it or not to be with this woman you’ll have to be better. She won’t allow you to be complacent. Eat right, put in the extra hour at the office, learn a different language. That fire that you’ve wanted under your ass is now sleeping sitting across from you at that new French restaurant.

While improving yourself is a good thing, be aware of how she’s treating you. If the way she’s motivating you is unhealthy, reevaluate the relationship. 

Pro #4: Your Chest Will Expand

Being with a woman who knows what she wants, is gorgeous, and is confident will rub off on you. You should be proud to be with such a woman. You know that she could be going out with any number of guys, but she’s choosing to spend time with you. How can such a trophy of a woman not bestow you with gut-busting confidence? 

High maintenance or not, being with an awesome woman should give you a confidence boost.

Pro #5: She’s Probably Fit & Healthy

The high maintenance stereotype places quite an emphasis on being healthy. This means eating right, exercising, and staying mentally fit. Who doesn’t want to date a powerful and beautiful woman?

And it’s not only her that reaps the benefits of a healthy lifestyle. As you two become more intimate her habits will rub off on you. Morning jogs and quinoa salads will replace sleeping in and fried appetizers. Dating a high maintenance woman might just mean living a healthier and longer life. So what if she’s over the top finicky when it comes to ordering her salad?

Pro #6: She’ll Age Better

Does she use wrinkle-combating cream before she goes to bed every night? Does she rarely eat sweets, always uses sunscreen, and works out even when it’s rainy out? Appreciate the time she puts into looking good. This investment will keep her looking good well into her later years. It doesn’t matter if you’re a woke dude that doesn’t place too much weight on superficial beauty. You’ll can still appreciate a nice face can’t you? 

Con #1 of Dating a High Maintenance Woman: If She’s Used To Daddy’s Credit Card, You’ll Have Less Disposable Income

She didn’t all of a sudden take a liking to the fancier things in life. Years of being pampered by her parents shaped her into the high-heeled vixen you’re currently dating. 


It might be difficult to wean her off the lavish lifestyle. Are you willing to step into her father’s shoes? Do you have the pocket size to support her tastes? Expect to eat out more, buy her presents, and even support her cosmetic alterations should she desire them. It’s not a given that you’ll be leaned on financially. But even if she can support herself financially, you’ll still end up spending more money on extracurricular activities such as fine dining, galas, etc. 

Con #2: She Might Replace You

I guess this is a ubiquitous fear when dating, but it’s especially troublesome when dating a high maintenance woman. HM woman are always looking for the next best thing. This is reflected in their entire lifestyle. She’s not willing to settle when it comes to her professional, social, or romantic life. If she starts mingling with a dude that’s better suited for her than yourself, she won’t hesitate to pull the trigger and ghost your ass.

Maybe that’s a bit harsh, but that’s the behavior that the stereotypical HM woman conjures. Knowing that she’s always looking to level up might be the motivation you need to keep striving to be better. If it becomes too tiresome constantly trying to win her over, drop out of the fight. Just because you need to fight for her doesn’t necessarily make her a keeper.

Con #3: You’ll Have To Wait Longer For Her To Get Ready

Remember dating in college? Neither one of you had money, time, or the willpower to put any real effort into looking good. Date nights revolved around events on campus and it would’ve looked odd if either of you decided to dress up for Wednesday night trivia. This girl isn’t going to be rocking sweatpants with your college logo slapped on them like your girlfriends of the past. She needs time and a steady hand to get ready. 

You might consider this a boon. She takes pride in looking good. Any man would be proud to have a dapper looking lady on his arm as you two strut your stuff around town. The time it takes her to get ready could also be viewed as much needed me-time. In this time you can read up on the news, continue your streak on Duolingo, or catch up on the newest Netflix shows. But that’s looking at life through rose-colored glasses isn’t it?

To avoid getting annoyed by her lengthy preparations, get accustomed to her patterns. If it takes her two hours to get ready, acknowledge this and take your time getting to her house.

Con #4: She May Expect The Finer Things In Life

Say goodbye to driving around town in your Prius, eating generic ice cream, and booking rooms at hostels. This woman has been vacationing at exclusive resorts since she was seven. Now that she’s got her own money and a man to boot she’s not trying to slow down. Be ready to blow at least 10k on a ring, jet off to other countries at least once a year, and eat out multiple times a week.

Should you two share an affinity for the finer things, this might be a match made in heaven. But not everyone likes to blow money on pricey vacations and good food. If you can’t keep up with her lifestyle and expensive tastes, perhaps find a compromise. If no compromise can be reached, it’s best to nip this relationship in the bud while it’s young. 


Con #5: Does She Make The Waiter Feel Bad?

Let’s call it like it is. She wears designer clothing, says she speaks French though you’ve never heard her, and insists on ordering lobster whenever she can. Am I describing someone that might think they’re a little better than everyone else?

Weed women like her out via MegaDating. Rude people can be quickly identified when MegaDating. The first date requires that no more than $10-15 is spent, and that the date lasts for no more than 1 hour in duration. MegaDating is the act of dating prolifically. By tapping various social streams you’ll be able to find ample single women to date.

Don’t settle for someone who’s mean to waiters just because they’re hot. There are plenty of beautiful women out there that have hearts of gold. Need a little help finding them? That’s where I come in. I’m no matchmaker, rather I’ll equip you with the tools you need to fish for yourself. A matchmaker’s pool is a bit confining. You’ll only be able to interact with the nominal number of fish within a tiny pool of water. But when you book a 1-on-1 Skype session with me, we’ll create a 360 dating plan that teaches you how to fish and hook all types of women, even including high maintenance ones.