I guess I would have been tempted to support Kennedy in 1960, Clinton in 1992 and 1996 and Gore in 2000 but in the end I think I still would have supported the Republican nominees. Supporting Clinton in 2016 wasn't a hard choice.
Perhaps Dutch elections would have been harder. I guess I might have considered CDA in 2002 (VVD elected a social liberal/centrist leader) and in 2003 (to prevent a social democrat from becoming PM) but I probably still would have voted VVD in both cases because the VVD always remains to the right of the CDA on issues I care most about. And PvdA-CDA cabinet with a PvdA PM probably wouldn't be much to the left of a CDA-PvdA cabinet on policy, but serving under a PvdA PM might hurt the CDA (and help the VVD
).
I guess in Germany I would be a CDU/CSU/FDP swing voter (but I'd generally support the FDP, especially now with Merkel as CDU/CSU leader).