If things are going well, which means we establish a joking, teasing conversational flow and repartee, I'll take a break at some point and either go to the bathroom or go to get more drinks... and when I return, I'll apply my initial, patented, split second, one index finger unexpectedly into each of her sides move.
If I get: "Why did you do that? I hate to be tickled?" I'll just shrug, charmingly say it was an accident with a grin, and move on.
If I get a positive reaction, I'll say with the same grin, "Obviously you feel guilty about something, and I'm sure to get it out of you somehow."
If I get no reaction at all, I'll think, "Ugh." 🙂
Thoughts?
Just throwing my two cents in here after reading all these responses. Let me ask folks this. Did anyone read that very first part of the OP's post? He put a caveat to his desire to tickle his date. He said IF things are going well and they establish a fun type of conversational flow, he might try to sneak in a tickle. So, he is not saying he will tickle her no matter how the date is going. He feels comfortable enough to even try it because the woman is giving off some kind of vibe for him to try.
I totally get why people would be concerned about the type of behavior the OP is doing. I get it. But, let's take it in context. If the date is going really well, they are having fun, they have chemistry, etc, for him to do a quick tickle is not exactly a crime. I read some of the responses about sex on a first date and how that is a "spur of the moment" type of deal compared to what the OP is wanting to do, which is premeditated. Um, not quite. If you wind up having sex on a first date, there is SOME kind of premeditation. For example, since we are all safe adults, how can someone have a condom on them (man or woman) without some kind of pre-planning? You know there is a possibility that sex could occur. "Not me! I don't think I will have sex on the first date!" you might say. Good for you. Now, realize not everyone thinks this way, otherwise no one would be having sex on the first date. It all depends on the two people, how the date goes, and how they interact will determine if there is sex or not. Same with the OP wanting to tickle his date. If the date is not going well, or he is not vibing with her, I doubt he tickles her.
I think we all need to chill sometimes. Honestly, the OP did not say anything that was too weird. The very first sentence:
If things are going well, which means we establish a joking, teasing conversational flow and repartee
tells me his desire is conditional. I know people love to overreact to things if you don't give a full confession to the woman about your fetish, then have her and you fill out a 35 page contract detailing how the tickling will go and have it notarized, but it all depends on the situation between those two people. Can we give some benefit of the doubt? If the woman loves it, then what harm happened? If she gets pissed, then the OP will lose out. For me, I like to throw in the question to a first date to find out if they are ticklish or not, but that is just me and my style. I guess that makes me "creepy" too, because I planned to ask them if they are ticklish or not on the first date. It is about reading the situation. Not everyone will be able to read it correctly, but some will.
Just wanted to give a different perspective. Believe me, if the OP said "I am going to tickle my first date without her expecting it" and left it at that with zero context, i will be joining in with the rest of you and chastising him. But he literally wrote there would be some kind of rapport that was established that allowed him to even try it.