I got this from Style;

When he tells himself he's not going to do something, like shit talk someone for a month or staring too long at a girl without a direct approach, he owes the person something.

Every time Style didn’t keep his own word, he gave away a dollar. But you can also think of different stuff
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How well would this work as an opening or midgame? It hasn’t to be money, it can be anything at all

For instance;

What if I have a conversation going with a girl and all of a sudden I take off my shoe and say; I promised myself I wouldn't think of *whatever it is* but if I did, I would take something off.

Or:

Damn, I ow you a dollar, cus' 20 minutes ago I promised myself I wouldn't stare at your *something you like about her* or else I would give you a dollar... You're costing me money, girl

I don't really think is a good idea. That's an IOI from you to here and, I think, a DLV too. Basically what it telegraphs to me is "I've been noticing you the whole night and I've trying not too look so far that I'm having to bet against myself... and I won!"