how appropriate?

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I don't think it'll be too creepy because the girl would probably get that he's shy without his clown makeup & is sweet unless she thinks he's a looner which is someone with a balloon fetish. The girl would likely say something like Thanx & go on with what she was doing unless she has a kid with her or is wanting to hire a clown for her kid's party. Otherwise the guy would have to make a move after she says Thanx

I didn't call you a creep. I said the idea is creepy, which it is. It seems extremely over the top and strange, and watching a guy fumbling with a cylinder shaped object at waist level kind of puts people's minds onto something else.

And to be honest, a lot of whether it's creepy or not has a lot to do with the guy doing it, and with the girl on the receiving end. Unfortunately, some guys could get away with anything, while others don't have that luck.

It's just my opinion, if you think it will work, do it.

Ahhh... Sorry hale_bopp. I misunderstood you. You're right, it totally depends on the individual.

I suppose I was imagining a different setup leading up to the balloon game. I imagined the girl and her friend sitting on a bench in a mall, near a balloon shop. All things that weren't described in the OP.

As I said, I am the kind of person that would do this.. it's very much in my whimsical nature, and when I think about it, In practice I would have sent a lot of subtle signals and looked for signs that she was intrigued before approaching her.. It's hard to describe I guess, but in real life I'm a very unthreatening looking person... I'm physically very thin and I guess quite "rubber faced" in a Jim Carey kind of way, and, so people tell me, have quite a cheeky, childlike expression when I'm having fun, which all goes to make it clear that I'm not a threat.

Also, being in my early 40s, the "girl" in my case would be a confident, friendly looking woman at least in her 30s, otherwise I wouldn't be interested in approaching her in the first place.

Please do accept my apologies!

Just my 1ct input: why not just going to that place with a bicycle? that would justify having a "pump".... and the idea of balloons is very nice, so whomever is planning to do so, go for it

As I said before, it all comes down to whether it is genuine or not. If that guy really likes that girl and respects her (that means not bothering her), there wouldn't be any element of creepiness to it.

You are contradicting yourself there. You said at first it was just creepy. Now you say it's to do with how they view it.

The first part was my opinion.
The second part is how the average women acts in general.

Two different things. If a guy did that to me I would think he's a bit weird no matter what he looked like.