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Thanx for all replies, I take everyones advice into careful consideration. I just want it to be natural instead of me seeming to bother her workout. I know that is SO AFC, but at the same time I'm not trying to be like all the other guys that probably hit on her at the gym. The other day, I had same headphones (situation), but the girl was doing a weird stretch and I used that as something to escalate... I use the IOI's plus situation, but I had nothing to work with in this without seeming random?
-plus she is a lot older
Older women have been through it all. They cut to the chase and do not require much. Well at least from my experience. I am pretty sure most guys do not go up to girls in the day time to hit on them, so you are already separating yourself from the pack.