See, if you asked me to go kayaking, I would think, "Hmmm - he knows me well enough to know what I'd enjoy and what I wouldn't. He'd never suggest something unless he thought I might have fun. So maybe I should consider it."
He (the date) is suggesting it because he likes it, with no regard for what I like. When I say I'm not interested, he tries to convince me otherwise. I think he means it to be encouraging – which it might be, if I said I want to go but I’m afraid. That’s not what I said. I said I don’t want to go – and trying to convince me that I do comes across as condescending, not encouraging.
I also know you, and I trust you not to leave me stranded in the middle of a lake if I can’t paddle, or I flip over, or something. So it’s completely different if you invite me, versus a guy I've never even met in person.
I'm all for adventure. I like to explore and try new things. I'm certain there are people out there who take bigger risks than I, but I'll always try to keep an open mind.
Like I said to Engineer, I'm actually not completely opposed to kayaking (or other, similar, outdoorsy type stuff). But, it's definitely outside my comfort zone. When I step outside my zone, I need to be with someone I know, and who I trust. I need to not be worried about making a fool of myself, or feeling vulnerable.
That's not a first date. A first date is about getting to know someone, and starting to feel comfortable. So asking me to go someplace I've never been, to do something that scares me to death, with someone I don't yet know how much I can trust? That's too much to ask for a first date.
Way too much.
Keep it simple, and maybe we'll work our way up to kayaking, or bike riding, or hiking, or whatever.
If you're really lucky - maybe I'll even take you shoe shopping one day.