How To Date A Tall Girl

[Image via Jesslee Cuizon on flickr.]

Yesterday a question popped into my Google Alerts, and it gave me a bit of a surprise.

Along with all the usual stuff like “why don’t men like tall women” and “is 5’8 too tall for a woman” (sigh)  was this gem:

… There’s a tall girl at my school and I think she’s beautiful … she’s a freshman and she’s 6 feet (I’m 5’8 and a Sophomore). I really want to get to know her and maybe later on ask her out, but I’m having trouble just going up to her and trying to start a conversation with her. I have her in one of my classes (the last period of school) . And I was wondering if anybody has some tips on how I can get past my shyness and just go up and talk to her. Thanks.

Isn’t this adorable?  I just had to butt right in there and share some advice.  I think this guy (Aron is his name) is just so cool and brave for not being worried about what his buddies will think if he dates a girl taller than himself.  Instead he just has all the usual worries and insecurities that make dating so nerve-wracking!!

I thought it might be fun to put an extended answer up here and let you guys help Aron out.  My first thoughts:

The first thing you should know is, never to be intimidated by a tall girl. In fact, she may be intimidated by you! Most tall girls have to get used to boys asking them out because it’s “hilarious”. Imagine going out and having drunk dudes constantly going “how tall are you?!” or the much more hurtful stuff like “That is one HUGE B#$%”.  Guys will try to get tall girls to dance with them, just to make their friends laugh.

For that reason, tall girls (especially younger tall girls) are often playing defense, second-guessing any guy who expresses an interest.  Is he for real?  Is he doing this to make fun of me?  If you think she’s not interested, maybe she’s not — but before you give up, ask yourself if she might just be trying not to get hurt.

When you do get up the courage to ask her out, do it away from other people so she doesn’t think you’re making fun of her. If you can’t be private, ask her out for coffee or something low-key. If she knows you’re for real she’ll be happy to make a genuine connection.

To make a long story short: height plus a bit of defensiveness can make us seem aloof and stuck up, but we’re only human.  At least we’re dressed that way until the mother ship returns.

Of course not all tall girls have these issues.  Your tall girl might well be a confident and awesome lady.  That’s going to make this a whole lot easier, because that kind of girl will be kind enough to just tell you straight up if she’s interested or not 🙂

Oh, and — when you are dating, please don’t get all embarrassed if she wears heels or if people look at you strangely.  Do what Mick Jagger and Nicolas Sarkozy do — OWN that you are out with a hot tall girl on your arm.  She’s a rare thing, a Ferrari amongst Toyota Camrys.  Not every guy is man enough to handle that.

[“I’m Mick Jagger.  Hot tall girls is how I roll.”]

But that’s only my two cents.  Tall girls — how do you like to be approached?  Any advice for that guy who’s dying to ask you out and just doesn’t know how?

Anne Shea is the founder of the Sarah Vain and Tall clothing line: find her at


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