How to Ask A Girl Out on the Trail

I slung drinks and hot plates in a trendy eatery for years, basically flirting for a living, without once being

If she’s running from you, give up.

I slung drinks and hot plates in a trendy eatery for years, basically flirting for a living, without once being asked out. But when I took up mountain biking, I could barely go for a solo ride without a guy at the trailhead chatting me up and, inevitably, asking for my number.

Though I’m still somewhat mystified that men show more interest when I’m covered in trail dust than neatly made up, several of my girlfriends have shared similar experiences.

I’m sure there are several reasons for this, but I’m guessing it’s mainly because it’s easier to suggest, “We should ride together sometime” or say, “If you ever need a running buddy…” than it is to straight-up ask a girl to dinner. It’s much less risky if it sounds like you didn’t really mean it as a date. You’re just looking for a trail buddy. A female trail buddy. A single female trail buddy.

But if you ever dream of doing anything off the trail with that cutie you met on the mountain, take some advice:

  • Just because I smile at you or say hi as we pass on the trail doesn’t mean I’m flirting or want to chat more. I smile and say hi to everyone on the trail. Including your grandmother. And Bernese mountain dogs.
  • Odds are, I don’t need you to help me fix that flat or adjust my bindings. Of course I appreciate the friendly offer, just in case I happened to have forgotten my tire levers or need an extra hand. But I’ll ask for help if I needed it. And if I don’t ask for help, I sure don’t need you hovering while I fix my mechanical – or, worse, butt in and try to take over for me.
  • If you’re thinking about asking me out, you had better be okay with me beating you to the top, or the bottom, or leading the climb. There is no bigger turnoff than a man whose ego won’t let him admit that a woman is faster/stronger/more skilled than he is.
  • Even if I give you my phone number in the parking lot when you suggest we “get together for a ride” or “go cragging” sometime, I may have no interest in an actual date. It’s wonderful to have a roster of buddies to hit the hot and dusty with, but I’m probably much more selective about who I would join for dinner or drinks.
  • Just because we share a sport does not mean we are compatible in any other way. A good friend of mine learned this the hard way when a four-year relationship fizzled, having been based solely on attraction and climbing. We may make stellar mountain-biking buddies, but if we don’t also see eye-to-eye on philosophy, literature and lifestyle, you and I will never make it past the parking lot.

Mountains can be great matchmakers. If you’re already sharing a trail, you have at least one thing in common. One beautiful thing. But if you’re looking to share something more, let it happen naturally. Be patient. Another outing or two on the trail will help clarify whether or not you two could could ever end up zipping your sleeping bags together.

Contributing editor Hilary Oliver lives in Denver and blogs at The Gription.
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Showing 24 comments
  • Michael B

    Thanks for the advice Hilary… Although, I feel the article would be more aptly entitled “How not to ask a girl out on the trail.”

    Nonetheless, good stuff.

  • twoeightnine

    Hey… would you… (kicks rock on the ground)

  • S.L.


    My tall, blond girl- who has hundreds of road, mtb, ‘cross, ‘track races under her belt and can kick most guys butt on the bike constantly has stories of guys trying to “help” her fix a flat or something. Usually they are lousy trail mechanics, and screw up a repair she could have done easily.

    It’s also hilarious to watch guys play “keep up with the girl,” only to have her slowly ramp up the speed while chatting away till they blow up and fake some sort of mechanical problem.

    Fit athletic dirty girls definitely attract attention. There are few of them.

  • Adam F

    Ladies…just because a guy says ‘hi’ or chats you up on the trail, doesn’t mean he’s asking you out. Often times, yes, but many of us are just as friendly as you and enjoy greeting everyone on the trail, including the Berner. So stop reaching for the bear spray and say hello to a fellow lover of the trail.

  • eightthreezerozeroone

    Most tough mountain gals around here are the opposite. Quote: “Just because I slept with you doesn’t mean I’ll ski with you!”

  • newman

    “I feel the article would be more aptly entitled “How not to ask a girl out on the trail.’ ”


    Thought this was going to be an instructional video. Nope. Just another GIRL POWER rant. Because the internet needs more of those.

  • Joe Jacobs

    I think you may be missing a motive. I think guys are often attracted to women who might share their obsession particularly if that obsession doesn’t have strong female representation. Having a partner who understands the need to get a ride or climb in is a particularly attractive proposition. I’m reminded by your article how lucky I am to have a wife who shares my love of sweet singletrack, tent nights and a good float. BTW, she kicks my butt on trail runs.

  • EcoHiker

    Good reminder I say. I really enjoy finding someone who you can connect with on the trail, but it’s not always going to be on a level deeper than your love for gear (so to speak). Be organic and have a piece of humble pie when you meet someone you might like on the trail, if things don’t work out at least you can have another friend to play in the dirt with. Cheers, beers, and the great outdoors!

  • Daniel

    Im with Newman on this one. Just typical…

    So tell me, just where is it ok to ask a woman out on a date these days?

  • David

    Agree with the above comments. It’s not PC to ask a girl out who happens to be doing the very thing you’d love to share a life doing. But while talking to single lady’s at the local bike club party, they are dying for it just like us. Why the contradiction?

  • Malcolm Daly

    So someone needs to print a cycling jersey that says, “Just because I sleep with you doesn’t mean that I’ll ride with you”. Or make it a t-shirt ans change ride to climb.

  • Sondra

    I don’t see this as a girl power rant if anything it is discussing equality in sports and the idea that women don’t need to be saved or coddled when they have a flat. We like to get our hands greasy!!

  • Mike

    I think the author needs to get over herself.

  • J

    ..funny, but I NEVER see any of you sweet things on the river twitching a 5wt…. and I’m real good with that!

  • Pete

    Twitter thought this site would be to my liking and directed me here. Too bad this was the first article I read. I have to agree with the others:
    “How not to ask a girl out on the trail.’ ”
    “Just another GIRL POWER rant. ”
    “I think the author needs to get over herself.”

    Got anything to redeem yourself with

    • steve casimiro

      I don’t know, Pete. Do you have anything nice to say?

  • Stoneman

    Hey guys, lighten up. This is just a humorous article giving some insight into the minds of action women. She’s giving you some tips; smarten up.

    • steve casimiro

      Thanks, Stoneman. Honestly, I’m blown away by the negative response to Hilary’s story. First, none of us guys know what it’s like probably to be chased from the time we hit puberty and how that would affect your response to future unwanted blandishments. Second, I didn’t find her doing anything but trying to be helpful. Third, girl power? Seriously, I don’t think Hilary’s the one who has to get over herself.

  • Pete

    The author won’t admit she chooses to feel victimized by her interactions with men in the backcountry and it seems men are the problem here, not how she sees the world. Maybe some introspection is called for here?

    Maybe an article called, “What I learned about me when I didn’t blame others for my experiences.” would show people real Girl Power and how to be a better outdoorsman/woman when interacting with others?

    Thank you for your comment Steve, yes I could have been nicer, I will temper myself next time.

  • Brett

    The basic rules for asking a woman out are as follows:
    Rule #1. Be good looking.
    Rule #2. Be good looking.
    Rule#3. Have money.
    Fail to follow these rules and anything you say to a woman is just sexual harassment.

  • paradise

    steve – thanks again for allowing a wide range of articles on the site. funny to see the boys get their panties in a bunch over an issue that is their own destiny to control…

    oh, and welcome new readers. don’t get jaded because this was your foot in the door.

  • Mtnlee

    Those suggesting the introspection mirror might want to take a peak into it themselves and take their own advice — “get over yourself”.

    Super article Hilary! Thanks for putting it in Steve.

  • jerome

    good points all above.
    think its a funny piece, yet hope there will be another post soon with the funniest/ best/most successful hook up lines on a trail. and if I (male, married, two kids) do smile at or start a chat with you, sexy runner lady, it does not mean I want to date. I may just appreciate an opportunity to take a break from pain or exhaustion or boredom.

  • will

    i want a dirty girl to ask me out!

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