I never feel
bad about overtaking or being overtaken, but if I'm overtaking I do feel sensitive to people's pride, and try to do it with plenty of space and not pedalling like I wanna be Lance Armstrong. I might be a bit miffed if I was overtaken on my road bike by a mountainbiker but that's never happened. However, if I'm on my mountainbike I get great amusement from chasing any roadies that aren't going fast enough! If people really get the hump about being overtaken safely, then they have personality defects that are not my fault
. I notice this especially overtaking 50+ blokes in sportscars and young lads in hot hatches (when I'm on my 1 litre Yamaha, not the Giant TCR!) I also sometimes notice that people who are dawdling about in expensive cars get humpy when I overtake them (safely of course) in my Skoda.
I usually say hello to people I go past if they look 'normal', so I don't end up looking like I'm the one who 'has to' overtake, but there's no way I'm going to sit behind someone for ?? miles if they're not doing a reasonable pace. (I'm often late for work anyway, why make it worse?). Bu if I think their pace is close enough that I'll look a tit for overtaking, then I let them carry on in front, but you have to decide how many mph you're prepared to sacrifice for politeness.
Our Saturday group went out today for 45 miles at a 19.5 average today so we did overtake a fair number of other roadie groups, which is always slightly embarrassing and can get messy if you get entangled. One bloke was in full Mark Cavendish kit and the guy I was riding alongside was sort of good-humouredly taking the pee "Oh, look, it's Mark Cavendish!" The net result of this was that said "Cavalike" then felt compelled to sprint past our entire group (and we were doing nearly 30!) before almost crashing into the back of two horse riders! By then he seemed to be too tired to catch up, and in any case had left his mates behind, so off we went again. That's a situation I wouldn't fancy getting into! I think all parties concerned took it all in good humour, but…
All in all, do it nicely and don't feel bad.
Most people aren't that bothered, they usually prefer to have you go past rather than feel under pressure to speed up themselves. Plus they might get to draught you for a bit, which may be fun for them if they're 'up for it'.