Originally Posted by genejockey

This often puts me in a quandary - I know that women, especially the fitter ones, often find male cyclists will catch them and pass them, then blow up down the road. I don't want to be That Guy. OTOH, there's the phenomenon you describe, where a stranger hangs out behind them making them uncomfortable. I don't want to be That Guy, either.

What's happened to me a number of times is that because I'm heavy, on downhill sections I'll roll up on women who look like they'll kick my ass on the next uphill, so I don't pass because I don't want to be the first That Guy, but now I'm behind them, sometimes freewheeling, trying to stay back far enough that I don't become the OTHER That Guy.