So, back to the question. Would it bother you if the girl your dating are wearing heals that makes her taller than you? what do you think about it?
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I'm in a similar situation. I am currently pursuing a girl who is taller than me in heels. And she loves her heels. I've only ever seen her once in flat shoes. But that's not the problem. The problem is that she wears those absolutely gigantic heels that give you about 5 inches extra height. It's not a problem for me per se but the problem is that I don't think she will be willing to give up her heels. I have no problem dating her if she's taller than me in heels, but I don't think she will be comfortable dating a guy who is shorter than herself when she is in heels. If she didn't wear heels she would be a good few inched shorter than myself. But like I said, I don't have a problem with her being taller, but I think she would have a problem with me being shorter. And another problem is she is extremely popular. She has a lot of guys who like her so she is most likely going to choose somebody who is taller than her when she is wearing heels, which leaves me with really no chance.
Anyway, there are a few questions you need to ask yoursef. How much do I like this guy? Does he like me as much as I like him? Do I like him enough to be comfortable around him with my heels on? Does he like me enough to accept me as I am? If you both like each other enough then I doubt the heels issue would present as much of a problem. At least not as much of a problem as the one I'm having.