I shouldn’t say it’s always hard for me to fawn.  I find it easy to fawn:

1. When I like the fawnee.  I guess that’s sort of obvious, but it probably needs to be toted out and examined.  Since I like the person anyhow, I don’t have to worry (as much) about whether they’re going to like me.  I don’t have to worry about what to say, because we already have things we like to talk about.  All I have to do is feature things they want to talk about rather than feature things I want to talk about, and we’re off to the races.
2. When I’m not fawning on my own behalf, but on behalf of a third party, like a Cause or a Product.  I don’t know why this makes fawning easier for me, but it does.  And not just me; a friend told me the other day he doesn’t mind fawning when it’s on behalf of a greater cause.  Maybe this gets to the heart of why fawning takes chutzpah: when you’re fawning on your own behalf, you’re saying, “look at me, look at what I want, look at what I’m after.”  That’s a chutzpah sink; it’s much easier when you’re saying, “It’s not about me, but about <Important Cause>.”

Fair enough.  Fawning is harder than usual for me:

1. When the fawnee is indifferent to me.  Now I not only have to say, “listen to me,” I have to act like a clown or make a fool of myself to get his/her attention.  I’m not sure why I equate drawing attention to myself with acting like a clown or a fool, but I do.  And to make a clown of myself and then have the fawnee ignore me: it’s humiliation++.
2. When I have to compete with other fawners.  Right here is why I hate networking events: many-to-one fawners-to-fawnees.  Good definition of Hell: I can be rescued from eternal torment in a lake of fire, but the Way Out is to fawn on Satan or one of his top lieutenants at a networking event where all the other damned souls from my lake are fawning to get out as well.