Dating a Tomboy vs a Girly Girl – Pros, Cons & What Do Men Love More?

Last Updated on January 9, 2023

So, you’re back in the dating world. Now the question is, what kind of woman are you considering dating? The age-old debate of dating a tomboy or dating girly girls is raging in your head.

Both have equally attractive qualities and some may even share characteristics, but which will be the best match for you? Today, we are going to look at the pros and cons of both. This will hopefully make the decision somewhat easier for you, but the choice is yours at the end of the day. Happy dating, and let’s get into it.


The difference between a tomboy and girly girls

Now you can probably make a pretty well-educated guess as to what the differences between tomboys and girl girls are. A tomboy is a girl who totally embraces acting, well, let’s be honest, like a boy, whereas a girly girl is a woman who acts mainly feminine in the traditional sense.

But just for the sake of clarity, let’s discuss each one individually before we do into the pros and cons of dating a tomboy or girly girl.

What Is a Tomboy?

The tomboy is that girl who, you guessed it, acts like one of the boys. She’s probably always been there, hanging out with you and the guys without giving it a second thought. She swears, can drink you under the table, and enjoys comic books, action movies, and cars.

tom boy 2

You’ve recently realised that she’s pretty easy on the eye under those baggy shirts and pony tails, and there’s clearly something feminine about her. But can you date someone who is basically one of your best friends who happens to be a girl?

Speaking of the tomboy’s dress sense, they tend to look for more masculine items when it comes to their dress style. These include hooded sweatshirts, leather jackets, a T-shirt and sweatpants, or even a full-on punk rocker look and definitely no high heels. The less said about their makeup skills the better.

What Defines Girly Girls?

As you’ve probably guessed by now, the classic girly girl is the polar opposite of the tomboy. In romantic comedies, she is always the gorgeous girl who catches everyone’s attention.

Every guy (or girl for that matter) wants to date her, as well as every girl wants to be her. Her hair and figure are always flawless, her makeup is immaculate, and her skin is constantly radiant.

beautiful girl

A girly-girl sense of style is generally associated with more classically feminine personality such as being more creative, emotional, and caring. This is seen in outfits with pink, yellow, and purple tones, as well as designs such as flowers and glittering decorations. Girly girls are most often seen wearing dresses, skirts, cute tank tops, high heels, and perfectly matched accessories.

Side Note:

Before we carry on to the pros and cons section of this article, this writer would like to address the elephant in the room, “Hi Elephant”. Seriously though, it is worth mentioning that we are looking at two extremes when it comes to girly girls and tomboys, hopefully without seeming wildly sexist in the process.

This writer does acknowledge that there is a HUGE spectrum of tastes, styles and preferences and everything in between that makes up all women. This article is highlighting the differences between the two specific types in a broad sense only, and in no way makes light of anyones life choices, as the saying goes: you do you honey.

The Pros and Cons of Dating Girly Girls

The Good Stuff

  • Skinny jeans, heels, short skirts, dresses, or yoga pants This girl is always trendy and gorgeous, no matter what the circumstance.
  • She makes sure her body is banging. She watches what she eats and is often at the gym, doing yoga, or going for a run. Be warned, if you’re dating a girly girl, make sure you can keep up because you will be going with her.
  • She’s a great girlfriend who will cook for you, clean your home, and look after you when you’re sick. She’s also an expert when it comes to snuggling.

The Not So Good Stuff

  • She’s a little needy and complains when she’s not the centre of attention.
  • It might take her hours to get ready. The finished product is great, but what sorcery is going on in that bathroom? It makes you wonder what she’d look like if she wasn’t doing all of that work.
  • Among the major challenges that people encounter while dating a girly girl is that she is gorgeous. Every man wants her. They would go to any length to get her attention. The thing to keep an eye out for with girly girls is that they are well aware of this. They realize that the time they spend on themselves is valuable. This is when you come into play.
  • You will have to give her this validation on a daily basis. Probably several times every day. You must ensure that your standards are as lofty as hers. You must appear to have spent an hour grooming and primping, look after your body, because a dad bod ain’t gonna cut it.
  • There is a lot to do to keep up with her demands. If you believe you meet the requirements, a relationship with a girly girl may be for you.

The Pros and Cons of Dating a Tomboy


The Good Stuff

  • She doesn’t ask you a ton of dumb questions during the Super Bowl or get mad when you get in a fight with an opposing fan at a game. In fact, she supports it.
  • Underneath the clothes though she’s a total smoke. She’s active in sports and goes to work at the gym to burn off the calories from her two guilty pleasures: hot wings and beer.
  • She’s not insecure about her appearance and has the libido of a man. That extra confidence is really sexy and they can be adventurous and even explicit lovers.

The Not So Good Stuff

  • Her taste of fashion isn’t all that great. She always wears skinny jeans, Converse, and baggy T-shirts, making it difficult to notice her body.
  • She’s never gotten along with girly girls, hence the majority of her buddies are other men. They probably have too, if you’ve noticed how attractive she is. There will always be competition.
  • She uses the phrases “bro” and “dude” in regular conversation, which reminds you of your bros and, well, a dude.
  • The advantages and disadvantages of dating a tomboy can really be balanced. One of the benefits of dating tomboys is that you can be yourself. It’s simple to have fun them in without fear of appearing too boyish. Tomboys want to meet someone with whom they can be comfortable.
  • Another issue that may bother you is the fact that she has guy buddies. She probably wont spend as much time with other girls since she is a tomboy. This means you must recognise that they are her friends and refrain from being overly controlling or envious of the fact that other men are around. It is possible for men to be friends only. You could have the same issue with jealousy as you have with dating girly girls.

The Tomboy or Girly Girl Debate

A tomboy is a girl who isn’t typically feminine; she is likely to enjoy the same things that guys are known to enjoy. She also really likes these things and isn’t interested in them just to avoid being like other girls.

Tomboys can still like girly girl things, it’s just not the core of their self-image. She might be really into sports and video games, while also having dresses and skirts in her wardrobe.

It all comes down to the guy in the end.  Some people like women who dress up, put on lipstick, and allow men open doors for them. Some men consider this to be “high maintenance,” and would rather date a tomboy. Choose the woman you want to learn more about. Talk to their friends without seeming suspicious. Do not attempt to act a specific way for the sake of others. It’s never going to work. Be yourself, and the rest will fall into place. To each their own

The Best of Both Worlds

The answer, like many other things in life, can be found in moderation. Many men are attracted to women who are both girly girls and tomboys, those who hare characteristics of both.

A woman who can work in a garage without makeup, know how to use tools, do yard work, play sports, wears jeans and a t-shirt, and drink beer is sexy.

A woman who can dress up in a black dress and high heels, wear makeup, and drink wine and champagne is also sexy.

Both of these in a single lady is unquestionably a turn one.

Breaking Stereotypes.

For taking on a traditional gender role, the girly girl involved is viewed as shallow, vain, dumb “less of a strong woman,” or even as promiscuous. Whereas the tomboy is portrayed as a bitch, a man-hater, or even ambiguously gay, for having fewer traditional feminine interests.

These are the very same negative stereotypes that are prevalent in popular culture. Remember those romantic comedies we mentioned earlier?

Final Thoughts on Tomboy vs Girly Girl

At the end of the day, whether you like a tomboy or a girly girl is a matter of personal taste. After your first date, you may discover that you disliked the girly girl wearing dresses and that the tomboy works better for you. Or the other way around.

We want women to be comfortable in their own skin. Many women consider dressing up and applying makeup to be a time-consuming nuisance, and they are rarely satisfied with the outcome.  Some women come naturally to it and love it, which is fine; but it’s a drag when women who don’t feel like it are forced to do it.

In our opinion, you should look for a lady who can communicate well, knows what she wants, and, most importantly, makes you happy.

Go with the flow in terms of their physical appearance. Both choices are appealing in their own distinct way.

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Amy Olson

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