Trying to Get a Woman to Wear Windpants

[Miss Betsy]

So as the title suggests, I want to send out some feelers to see if I can get a woman to wear windpants. There’s a cashier at this gas station I go to on my lunch break for my caffeine run. She’s admittedly cute and she always makes small talk and makes the customers smile. It’s fall now so of course it’s getting cooler out. She’s worn sweatpants a few times. One such pair were a little shiny and from far away, looked like windpants. I’m looking for a way to bring them up in conversation and see if she has a pair and if I can get her to wear them. I’m thankful for any advice

 

[Fijawolf]

The next time she wears them, say that they suit her and if she wears pants like that often, then we'll usually start a conversation

 

[Miss Betsy]

Well, she’s never actually wore any windpants, they were just shiny sweatpants that looked like windpants from far away.

I did some brainstorming yesterday and maybe this might work. She’s super friendly so I might talk about how I went shopping this weekend and show her a picture of some new windpants I bought and let the conversation develop from there

 

[Fijawolf]

Try it like that and you'll see if you succeed. I'd like to keep you updated. I'd be interested to see how it goes

 

[Miss Betsy]

Hopefully it’ll be a good update

 

[shiny3stripes]

Well, she’s never actually wore any windpants, they were just shiny sweatpants that looked like windpants from far away.

I did some brainstorming yesterday and maybe this might work. She’s super friendly so I might talk about how I went shopping this weekend and show her a picture of some new windpants I bought and let the conversation develop from there

why not go one further and take them with you rather than a pic or better still.... just buy her some

 

[Miss Betsy]

Well I wouldn’t buy her some since we aren’t dating. She’s just a very nice cashier. I would wear them In front of her if I wasn’t on my lunch break. At work. I work in an office so I have to dress somewhat nice, at the very least corporate casual

 

[Noah267]

Yo, honestly, if you wanna talk to her, starting with clothes might be kinda weird, Just keep the small talk flowing – like about the weather, work, usual stuff, and maybe the topic will come up naturally, if you force it, it might feel awkward, you know?Take it easy! Ps But hey, if you really wanna mention those "almost windpants," just ask her where she got the sweatpants from, like you’re looking for something similarThat’s smoother 🤠

 

[Bella075]

You could casually compliment her style and mention how comfortable windpants are for fall. Try asking if she owns any or if she likes wearing them. Keep it light and fun—focus on the comfort aspect rather than pushing her to wear them. Good luck

 

[Miss Betsy]

I like that! Being pushy is never good so I never try to do that. I might try to say how I got lucky shopping over the weekend and then show her a oucture of them. Just the pants, not me wearing them. I’ll see where it goes from there

 

[Ala166]

Start with a light conversation about the weather and then mention how nice it is to wear windpants on cooler days. You might say something like: "I've noticed a lot of people wearing windpants; they're so comfy for fall!" This can open the door for further discussion.It’s important to be subtle and not pushy.If she shows interest, you can ask if she has any in her wardrobe. Remember, the key is to keep the conversation natural and enjoyable for both of you.

 

[skates76]

I'd be tempted to wear a nice pair of nylon pants as part of a casual/ urban outfit in her presence, maybe on the way home one day. I think a lot of people notice the swishy nylon clothes and want to feel the material.

 

[Cubitus the misunderstood]

Hmm, but now I have to get involved 😅

I would be interested to know if you have had more contact, verbally? So do you know each other a little or is this a completely foreign level?

To be honest, I don't have any real experience with this exact topic, but I do with girlfriends, so just friends.
But in my case it's also the case that we already had a common theme, e.g. sewing or outdoor... These two topics definitely fit quite well. In the end, we talked about the material, difficulties in processing, weight, durability, etc... I like to add that it's not only very practical but also wears well or feels good and then I see what the reaction to it is... If the reaction is positive, I like to get, for example, a *pants reaching* "try this" .... Works, but hasn't yet brought out the nylon fetishist/in to me. (If we were at my place)


In your case, @Miss Betsy, it's a different story, of course, but I think if you're already making small talk then just ask her about these pants because you liked them... "Blah blah ... I like clothes like that, preferably vintage, but some of today's manufacturers are also quite good..........." That would be more or less my shtick....

 

[Miss Betsy]

Everybody’s given me great advice so far. This is no exception. I like the whole talking about how I would prefer vintage but some of todays clothing companies make things that are similar. I never would’ve thought to approach it from that angle

 

[Lyrch3451]

Reading through past replies gives me an idea so here goes. You mentioned she’s friendly and outgoing and also sounds like you two have already broken the ice so what I’m proposing is invite her to coffee the next time you both are free. If she agrees to that and have good conversation during coffee, spring the idea you two go for a walk in a nearby park or trail. When you go on this outing, wear a pair of Windpants that stands out the most, the more unique the better. I’m personally thinking the silver adidas ones. Chances are she will inquire about them starting the conversation. Then like previous replies suggest, pitch the benefits of Windpants. Then it can be “I have an idea, let’s do this again only next time let’s go shopping and find you a pair”
On the other hand if she doesn’t comment on your pants you could casually bring it up in conversation or leave it be and at the end of your visit say “ this was fun let’s do this again” and wear the same pants or a different unique pair on the next outing. If she’s curious, sooner or later she will ask about them.

 

[Miss Betsy]

Well I don’t want to sound like I’m asking her out, haha. The only way I’d be able to wear windpants in front of her is if/when I bring a change of clothes to work. I only do that when I have a concert I’m going to afterwards. I have one in a couple of weeks so I could do that

 

[Lyrch3451]

Oh yeah wasn’t thinking of it that way but now I reread what I wrote I now see that could be interpreted as asking her out. I guess that approach would only work if she knows you’re already attached and the understanding is it’s just a way to make new friends.

 

[Miss Betsy]

Yeah I never told her about my girlfriend or romantic life. We only have time for small talk