Asking Girls Out Randomly Can Sometimes Be The Only Way?

[Dash of Englishness]

Please tell me where this may have been discussed on the site before, if it has. I've noticed that a certain amount of situations involving attractive women/girls that I end up in, are often just that little bit shorter than I would prefer. As in, if that same interaction were due to naturally last a tiny bit longer, I'd have enough time to make a move on the girl without it seeming forced. A lot of such interactions I've had occurred during various jobs when dealing with the public when someone might need assistance. So in these cases I view it as if I get enough time to make a good impression, and make a connection, but (as it's destined to be a short interaction) not enough to ask her out. Obviously if I bumped into that girl later that week, then great, I've got something to work with. But it usually only happens that way in the movies. So in a moment like this when I feel I've made a good impression, if I force it too much I feel that the girl might think "oh, so you think because I laughed at your joke, it means I'm going to go out with you?".

The last time this happened to me was at the start of a triathlon just before the swim section. Me and an attractive girl were both late getting to the starting line (hoping it wouldn't start without us) as we were jogging along a little path to the beach. I said "I'm glad there's someone else as unorganised as myself", and we had some chat. When we got to the beach area near the starting line, I explained to her how to attach her timing chip properly, which she was struggling with. But I then decided to keep moving on into the water to get out near the starting line to put myself in a good position. I could've actually decided to forget all about my bloody race times (I don't take it too seriously anyway) and instead made sure to help her as I'm sure I could've built more connection in that time. Of course I got on with the race and never saw her again.

Now obviously if you approach a woman in a club, or during day game, it's perfectly okay to try and prolong the interaction as much as you can, but I'm talking about an interaction that were destined to happen regardless of whether you wanted it to or not. It hurts more when you throw away something that fell into your lap, so I think what it boils down to in these situations is, is the person comfortable making his move if he knows it may feel unexpected to the girl, or is he going to throw away the opportunity. If he is okay with the former, then what is the worst case scenario? I think the worst scenario for me is that I end up being viewed as a harmless perv by someone, which granted I might not feel too good about, in the immediate aftermath, but overall I'm okay with.

I'd like to hear your view on this. I think some of why I'm saying it is because I somehow feel a lot of what I read on this site leads people to believe there is a perfect system, but often there isn't.