Top tips to get you asked out by teenagers

I’m a twenty-seven year old gal who’s had more teenagers (or those freshly out of their teens) ask her out in the past six years years than, well, the entire time I spent as a teenager.

Now, in the sake of full disclosure, I was a pretty unfortunate looking person for a good chunk of my adolescent years – but even after I got hot as hell, I was still the one making the first move at the beginning of my relationships.

(This, I’m sure, is because people were so amazed by my overall transformation, that they were unsure as to whether or not I was the same person they used to know.)

I kid.

Kind of.

For serious, had I not had ovaries the size of basketballs, I would still be languishing in a sea of unrequited crushes, being tossed about by white-capped waves of sexual frustration.

I was a champ at asking people out (the two times I did it.)

Now, since I wrote earlier this week about how a twenty year old boy asked me out on skytrain last Saturday night, I’ve had quite a few friends ask me what exactly it is that I am doing to have this be a semi-regular occurrence in my life.

I didn’t have a coherent, non-self-deprecating answer at the ready, so over the past few days I’ve given this query some thought, and think I may come up with a probable (but perhaps totally erroneous)  hypothesis.

However, in the spirit of science, I’m forging ahead.

Ladies and gentleman, (but really ladies, because, well, I am one of you) may I present: 

Top tips to get you asked out by teenagers*.

*or those in their early twenties.

1.)    Ride public transit. Ride public transit all the live long day. Not once or twice a week – we’re talking multiple times a day here (and weekends too). Teenagers, for the most part, don’t have a ton of money, so if they need to go anywhere, they take the bus, or the skytrain, or subway, or streetcar, or what have you.

Duh, duh, duh, another rides the bus...

I ride transit all the damn time, so it’s inevitable that I’ll find myself sitting next to someone whom I could have babysat ten years ago, had I not  instead chosen the high school career of Safeway cashier. And because of this inevitability, it is in fact unavoidable that at some point one of them will strike up a conversation with me, and before I know it – BAM!

They want to take you me out to coffee (at bloody 7:45 in the morning.)

2.)    Wear quite a bit of colourful clothing. I notice more and more just how varied in hue and tone my wardrobe is compared to most of the other people who work down town. When I exit the train every morning, and the station is flooded by a stream of black, grey and brown, I am the bright red life boat, carried along by the push and pull of the tide.

1 coat, 2 coat, red coat...

I don’t necessary think that it’s my clothing per say that’s getting me asked out, but since I’m not afraid to experiment with, and wear a ton of colour – in addition to taking different risks with my outfits (wearing traditional mens clothing, and mixing formal with casual pieces) – my style seems to attract a younger demographic.

Teenagers in general like to make comment on my choice in clothing and, or colour palette.

Animal print and stripes.

Then they want to take me out to coffee to talk more about my fashion sense.

3.)    Read science fiction and/or fantasy books. My only caveat being – please, please for the love of pete, read good science fiction and/ or fantasy. None of this Sword of Truth/Sword of Shannara bullshazzle.

That will get you disqualified right out of the gate.

(However you’ll gain ten points if you read your sci-fi books on the bus.)

But to get back on topic: teenagers always want to talk me up about the books that I’m reading, but particularly if they are of these two genres. They want to talk to me about A Song of Ice and Fire (even back before it got all HBO-ed and coolified); they want to talk to me about Terry Pratchett; they want to talk to me about Richard Matheson. (Okay, so that last one’s more horror that anything else, but we’ll have to let that slide.)

Even Mr. Penguin wants to talk about Game of Thrones.

They want to talk to me about books and then take me out to coffee to talk about books some more.

4.)    Laugh to yourself. Whether you’re walking down the street, riding transit (seriously, RIDE IT!), sitting in a coffee shop, or waiting in line at the grocery store, be so completely lost in your own thoughts that you bust up your own gut like a busting thing.

I love to laugh. ALL THE TIME.

Older people will think your completely bonkers (and rightfully so) but teenagers want to know what’s so funny.

And they’ll want to take you out for coffee.

5.)    Quote the crap out of movies and TV shows. I was on transit once (did I mention that you should probably ride transit?), talking on my mobile, TO MY HUSBAND when I said, “that’s, just like, uh, your opinion…man” and the fella sitting to my right, spoke up literally, the second that I  hung up, wanting to talk more about the Big Lebowski (aka re-enact the whole movie for the remainder of our ride.)

And then he wanted to go to a coffee shop, to re-enact our re-enactment – just in case we missed a part!


He was pretty surprised when I declined, citing the fact that I was, you know, a married woman.

Which brings me to my last point:

6.)    Wear a wedding ring. First, teenagers don’t look for wedding rings, so they are basically a moot point. Second, the longer I remain married, the more teenagers ask me out. And third, most of the teenagers who’ve asked me out haven’t cared when I told them that I am forever removed from the dating scene.

Ring around the rosie...

They all want to convince me of the reasons why I should no longer be married.

Over coffee, of course.

So there you have it ladies – six, very simple tips on how to increase the number of your youthful suitors.

But, let me finish off by saying this. Don’t wait around for someone else to make the first move. If you like somebody, go-go-gopher it.

It’s always better to know, and heck, if they like you back? Well, there’s no better feeling in the world.

Seriously, I’ll tell you more about it.

Tea anyone?

Published by

Vanessa Woznow

Writer, runner, ranter, reader. I write about all things.

28 thoughts on “Top tips to get you asked out by teenagers”

  1. Okay, this was absolutely hysterical! I can see how you would draw in the younger demographic though – fun, full of life, bright, happy, and humor in one package! If you said yes to all those offers you’d be drinking coffee at all hours… ;)
    Kind of funny how we get older and then get noticed. I’m going to hope there’s something in there about only being as old as you feel and aging above and beyond gracefully.

    1. I’d never sleep! Juggling multiple boyfriends is a tough exercise…

      Awww, you’re making me blush with your lovely words! (Obviously we’ve never met in real life…haha)

      It is funny isn’t it? And I totally agree with you – you’re only as old as you feel!

  2. Hmm the only attention I get from teenagers is drunken assholes from (insert suburb hear) yelling out the passenger seat Friday nights on Granville St. (I wouldn’t go there if I didn’t have to in order to get home!)
    Maybe it’s because my entire wardrobe consists almost solely of brown, grey, and beige ;)

    1. I’m sure some of those jerks are home grown Vancouverites. (This, of course, doesn’t excuse their actions – I’m just an sucker for equal opportunity blaming).

      The day you ride skytrain, in a red dress, reading Bradbury, the entire teenage population of the GVRD won’t know what hit it!

      1. Of course! Usually when I see young people driving cars downtown, I assume that they’ve come a long distance, otherwise they’d just walk/transit :) But yes, Vancouver had plenty of tools itself. I think I’d just like to do away with north Granville St in general…If not for the excellent music venues like the Commodore and Vogue.

      2. Right! I was going to ask you…a few posts back you mentioned being an ENFJ – did you take an “official” test, or an online quiz? I’m pretty sure I’m INFJ, but personality tests are fun!

  3. Haha, a great list of tips! So funny how in high school it would be amazing to be asked out on the bus but now it just makes you laugh and write about it.

    I am all for making the first move too! Good work! That’s why I’m crap at giving single people advice because it’s always the same advice as you gave above – go-go-gopher it!! (Not that I think it’s bad advice but clearly it’s still not quite the norm for the gal to be sticking her neck out to make a move.)

    1. Totally, totally agree. What I wouldn’t have done to be asked out – anywhere – when I was sixteen years old!

      I’m digging your style – maybe We should start a “first movers” club? Co-presidents?

  4. SO have to agree! Even though I’m not married (not even close to it…), I seem to do things or say things that attract younger men. The last one was even under age – and he thought I was 6 years younger than I am. Which would have still made me 6 years older than he is. I think it’s flattering, because obviously they don’t think you’re boring or old or lame.
    The book thing is SO true! I read a lot of fantasy and that always got them interested. Also a good one is if you’re good with computers. And that holds true also for older guys (read: guys my age :) ).

    1. Right on ChMarie! Glad to meet a sister-in-arms re: teenage suitors and fantasy novels! (I’ll have to work on my computer skills though…)

      Thanks for your comment and for stopping by!

  5. I was walking past teenagers in the mall and as I passed, one boy of the group practically chased me down to tell me I smelled really good. As if that wasn’t flattering enough, this happened 3 separate time at 3 malls in 2 states. Always teenage boys and always yelling loud enough to wake the dead – one boy even came outside as I exited the mall just to tell me I smell beautiful- which is ironic since ‘beautiful’ is the name of the fragrance I was wearing.

    1. Hey Dreamlife! You must smell amazing (er, I mean, beautiful!)

      And you are right about teenage boys speaking loudly. I think it must be because they are REALLY ENTHUSIASTIC!

      Thanks for the note :)

  6. I won’t lie; if I wasn’t older than you and hadn’t been perpetually attached from the time I was 19 to The Present, what you’ve described here could have been me (though I was never a homewrecker or awake at 7:30). I love when a woman’s style is somewhat (or completely) outside the norm and totally dig anyone who seemingly randomly references good movies. And ladies that are into scifi/fantasy/comics tend to be woefully outnumbered and nerdy gents like myself tend to pounce (although I converted my wife little by little). Although, for me, it doesn’t even have to be good. Ten years ago when I was 18, if I had seen a girl reading Fantastic Four or Superman (comics I typically loathe) I would have attempted some sort of flirtation and I spent my youth gorging on bad fantasy novels by R.A. Salvatore so I wouldn’t have judged you based on quality so much as there was a sword or a sweet unicorn on the cover.

    1. Alright “team been with the same person since teenagehood” – we are few are far between!

      Reading comics/graphic novels is such a great way to strike up conversations with people. I love when people are really passionate about their literature of choice.

      “I spent my youth gorging on bad fantasy novels by R.A. Salvatore” – this is epic. I spent my early teenage years reading all of Anne Rice, so definitely no judgement here!

      1. Oh Anne Rice…Charlaine Harris and Twilight/Vampire Diaries people should be sending her royalty checks for stealing her sexy vampire archetype. At least True Blood has the decency to have Eric Northman kill people instead of go to high school to pick up chicks like the other pop culture vampires these days.

      1. “I’m old enough to be your mom..” K, not really, but I’d love to say that and realistically, mentally, I probably am.

  7. This is very diabolical of you haha. Play with others your own age! Haha just kidding. Oh my gosh…I can only imagine how awkward things can get and how fast it gets to that point.

  8. Alright I am probably going to receive some heat for this post but I believe in doling out the truth in the purest form I can muster. So here it is…. the master tip…. to get you asked out by more teenagers (and men in general)

    7) Work on your looks

    Lose some weight, maybe work out a bit to tone figure, feminine hair styles (long hair not these boy-cuts), OR if you’re lucky wait for the inner woman to blossom etc…


    Speaking from the male point of view I’ve seen a lot of late-bloomer women who seemed like ugly ducklings growing up (late bloomers) only to become voloptuous heart-breakingly beautiful women later on. You yourself are admittedly one as described in the quote below from your post:

    “Now, in the sake of full disclosure, I was a pretty unfortunate looking person for a good chunk of my adolescent years – but even after I got hot as hell, I was still the one making the first move at the beginning of my relationships.”

    I dare argue that sole point above is what got you the attention you are getting today – NOT the things you’ve done or described in tips #1-6. Most men qualify solely on looks at the first impression. We’re biologically wired that way. #7 – working on looks gets you on the male radar – otherwise you don’t even register – it’s like pigeons or a fire hydrant in the background – you just don’t exist admittedly – don’t register in the conscious mind. A lot of these late blooming women Ive asked did absolutely NOTHING from their point of view and somehow they are suddenly inundated with the attention of men. Since one cannot readily observe themselves (its a psychological blind spot) we depend on others to tell us what has changed. They just started looking better on the outside from the male point of view. It sounds extremely harsh but this is how most males work and it is important to understand this fact to maximize one’s chances if one looks to get more male attention.

    Furthermore those teens asking you out did NOT absorb the full depth of your personality and being in that 3 minute run up they plowed through to drop the “I’d like to see you again…” payload. If it were all about personality then these short minute encounters are hardly enough to even begin to grasp who someone really is. Men and women alike like to think people will love them for who they are on the inside. I think this is true in a sense once you spend enough time together to get past the love infatuation stage. Otherwise no one will be hooking the opposite sex with their inner charms alone in such a short impersonal timeframe unless they are psychic or a good person-reader (and even then…).

    Those women who seemingly did nothing and got more male attention got hotter – that’s all. #1-6 may help generate interest but it is hardly enough to even initiate the approach in most cases. Many men are likewise driven by their testosterone – thus if she looks good – and the erection happens – they will most likely approach to satisfy their inner need often times regardless of what she may be doing or what she is like on the inside.

    To conclude I don’t mean to sound like a troll but from my vantage point this is what I’ve seen as getting results. My goal is to unify the discrepencies between male-female relations by really getting down to what each side of the coin truly wants. Men want beautiful women. Women want real MEN (strong, confident, knowledgable, alpha) not these bumbling/supplicating ‘afraid to rock the boat’ soft-spoken metrosexual types often running around these days. By working towards what each side in general truly wants (always some exceptions I have to account for/fetishes/etc) we can all help improve relationships between the sexes.

  9. for me, it did not work. i didn’t receive any positive response… ever. wish i had seen this tips before. never mind, i m gonna apply these next time… :-)

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