Cliff - Diego, because if anyone could survive it, he could. And he'd probably have a parachute. And because she could stand killing him the most, unfortunately.
Shag - James. Because it wouldn't be awkward afterwards at all.
Marry - Bran. Because she can't kill him and she couldn't deal with a LND scenario of a one-night-stand and frankly, she's doomed to it anyway since she has no Raoul.