Did you just snag a date with a tomboy recently and have no clue what to do next? Well, for one thing, dating a tomboy feels very different from dating a regular chick. For those lucky enough to be going out with this very special lady, we give you 10 great reasons to do so and survive the experience.

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When you date a tomboy, it can go both ways. It could feel like you’re wearing an old familiar pair of ripped jeans or doing prize-winning equestrian gymnastics on your Arabian thoroughbred. I’ll take the former to spare that lovely Arabian horse from pain.

Either way, whether you roll the classic, rock or hip-hop tomboy joint, tomboys will always be tomboys and most people (men and women) who find tomboys attractive may find themselves scratching their heads on occasion, trying to figure out why they decided to go out with a tomboy, least of all how to date them in the long-term.

That’s because we’re the girl all guys like to hang out with since we’re highly skilled in ‘bromancing’ male counterparts but we’re also the girl most girls find suave, cool and confident – if you bat for the other side, of course.

Whichever way you swing sexually, if you’ve got your head slumped in frustration, don’t worry. Tomboy Tarts is here to the rescue with some spiffy advise we hope you can use.

First, let’s recap what a classic tomboy is: She is, first and foremost, a woman who engages in a lot of activities or tastes usually dominated or engaged in by males. She resists anything that remotely resembles ‘Barbie’ and ‘pink’ and she has a natural aversion to tea parties, looking like a Stepford wife or spending the entire day glaze-eyed in a shopping mall.

All the above is also why bonding with a tomboy is not like bonding with a regular chick because 1. we are a little ‘out there’ with our take on life and 2. our attitude and our fashion sense is gender fluid, so you will not find us in a flower dress and Lady Gaga heels anytime soon because to our practical (and safety-oriented minds), those are reserved purely for circus acts.

We’re also not likely to be mushy, expecting sonnets to be sung to us on Valentine’s Day (sorry Celine Dion!) with a bunch of flowers stuck between a set of dentures (Oops! Sorry – we meant teeth!). Those kinds of gestures make us feel way awkward if not, slightly puke-ish. Excuse me. I feel the need to hurl right now.

OK – I’m back.

Now, with regards to why we are the way we are, I hate to say it, but we don’t have any answers. It could either be programmed or just conditioned personal preferences. Who knows? However, when it comes to giving you a few tips on how to date us, that – we can definitely help with!

So get your bowties and brogues on, here are a few tips on how we roll…



OK, so flowers are what the ‘girly girls’ are into but not all tomboys are into flowers (certainly not us at Tomboy Tarts), unless we’re scouting the great outdoors, botany style, in search of that rare specimen of flora. Flowers can also cause allergies. No – to a real tomboy-spirited woman, we prefer something that surprises us. What that is, is very subjective again. It could simply be a road trip, a new gym bag, a pair of dumb bells, a pair of sneaks, organic snacks, a new piece of tech or a binge night on the couch watching all two seasons of Daredevil.

Just about anything but them flowers. That’s just not our thing. Atchoo!



Every girl who has the tomboy spirit etched deep within her soul knows that nothing will kill her fire more than taking the conventional route. A typical tomboy takes pleasure in hiking the road less travelled, literally. Never mind the pitfalls, bumps and bruises she takes along the way because to her, those experiences are scars she wears proudly in the name of wisdom and experience. So forget the jaunt to the shopping mall. Bring this woman on a hiking, camping or fishing trip, on a weekend climb to the Kilimanjaro, go-karting, skateboarding or even planking on urban streets. If adventure isn’t your thing, then keep it simple with road trip, a wine tasting session or a comic con at a town near you.

The thing is to maintain an element of fun and surprise that a conventional girlfriend relationship lacks. Your tomboy crush is ready to try something new, something different and dangerous and she’ll be ready at the door with her backpack.



Tomboys are straight-talking women who don’t come with a license to BS. So cut the crap and get to the point or we’ll shoot you down with our candour. We don’t like beating around the bush because 1. It’s an effing waste of time and energy. 2. It’s an effing waste of time and energy.

You get the picture.

We can be brutal with our honesty but we hate the dramatics that come with it, so we are of the opinion that if we can dish it out, we are mentally prepared to take the brunt of our strong opinions. Also, most people assume tomboys rarely complain but I know a few queens out there so I’ll be pragmatic and say, yes, we have our grouses but we either take action to solve them or walk away from them if nothing can be done about it.



You’ll find us bungee jumping off a cliff before seeing us slumped against our lover’s shoulder in a theatre watching ‘Pretty Woman’ or ‘Me Before You’. By all means, leave the romance to Julia Roberts and her bee-stung lips. Tomboys prefer to express our passions despite all the stereotypes that we’re cold fish. We’re not. We’re just realistic, pragmatic gals and want our relationships to be fun, spontaneous and heart-warmingly sincere and genuine. Most of us wear our hearts on our sleeves, so ditch the rom-coms and bring on the superhero and action films please!



Tomboys rarely find it comfortable to be in the ‘damsel in distress’ role. We’re warriors at heart. In fact, most of us rarely like to ask for help because we’re very independent women who prefer to fight our battles without bothering the rest of the world with our troubles. We will tell you about what’s happening in our lives but that doesn’t mean we want you getting involved in it unless it’s requested. Even then, it has to be an exceptional situation because, well, heck, we have a helluva lot of pride about our independence. If you sense something is bearing heavily on your tomboy lover’s mind, the best way to handle it is to ask directly. If she is OK with your suggestions, then follow it up with an open offer of help. PS: At no time should you make her feel vulnerable or retarded when offering help, you hear?



This does not applies to all tomboys but within our realm, there are some extremely competitive tomboys. She could kick your butt at sports, out-swear and out-drink you when challenged. She could probably leave you in the dust playing ‘FIFA’ or ‘Assassin’s Creed’ on the PS4. This subset of tomboys are also probably fitter and faster than you and she has no qualms about beating you at anything you’re good at. Your best chances at surviving such a relationship is to not just let her win all the time but to keep the spirit of the game at its most competitive. It’s OK –she can handle the pressure. Just don’t let her see you cussing in the corner when she pockets in the winning shot at the pool table.



Now, we’re not endorsing the fact that tomboys are willing to live with a serial killer, abuser or rapist. We’re just less prone to holding off judgement on a person’s shady past or present, provided it does no physical or emotional harm to another human being. Rest assured, in the church of truth, you can tell us anything and everything that’s imperfect about you. Were you a failure at school or have a lot of unhygienic habits? No problem. We understand. Such things don’t phase us out or send us out the door screaming. For all you know, we might just be as unhygienic and gross as you and in the grand scheme of things, that evens out the relationship pretty nicely. In the end, it’s all about being aware, compromising where you need to, taking responsibility for yourself while owning up to your flaws are the most important things. The rest is just about finding happiness and joy in your dating relationship.



A tomboy does not spend 3-4 hours dressing up unless we’re playing a hobbit in the next ‘Lord of the Rings’ trilogy, prosthetics and all. This means you no longer have to wait for eternity for her to get ready before you go anywhere. In fact, a tomboy is always up for a challenge so if you give her a 15-minute dress up deadline, you can be sure she’ll be done in 5. I mean, how long does it take to throw on a pair of jeans, tee, hoodie and a cap, eh?



People, when you date a tomboy, remember you’re not Captain Picard of the Starship Enterprise commanding a whole unit of space troopers. So leave your passive-aggressive personality at the landing dock. Tomboys hate a ‘Cling-on’ and we don’t mean those extra-terrestrial humanoid warrior species from a galaxy far, far away either.

The more possessive you are with a tomboy, the more you’ll start looking like a real Klingon. Worst of all, your tomboy crush will find ways to slip out of your life if you display any signs of being needy. Tomboys are independent so space is important to her. Rest assured she will give you yours as well, so remember to return the favour and you’ll earn more relationship karma points.



A tomboy knows boys very well and they definitely know how to handle their lame jokes and often bridge the gap with other boys in your group. They enjoy the company of males and earn bonus points with the group with their ability to think beyond just cooking and shopping.

However, guys being guys – many will feel threatened. When that happens, the good thing is, tomboys will back off and ply their winning personalities elsewhere to more embracing male company. They might feel slighted at first but they’ll dust their shoulders and get back up on that horse. Your job, if you are dating such a tomboy, is to make sure that the vibes are always positive. You don’t have to defend her if some douchebag in the group starts getting sexist – your tomboy can definitely give them a piece of her mind – just make sure your group of friends aren’t assholes to begin with in the first place. While your tomboy lover isn’t quick to judge, she is so confident about herself, there’ll come a time when she’ll draw the line about being “one of the boys” or merely being a “joke” or objectified. She doesn’t need such abuse and neither does she need to be validated by your male friends. She is too cool for that.

If you’ve dated or are dating a tomboy, hold your horses and tell us about your experiences in the comments below!