Eleanor Roosevelt wanted to be loved. It's that simple. Start there and work your way out.
FDR loved no one. No one. Everyone was expendable at some point. Eleanor was expendable, Lucy Mercer was expendable, LeHand was expendable - she's the one that said FDR was incapable of true friendship with anyone -, everyone was expendable. He adopted and cast aside people no matter what it did to them. James Roosevelt blames FDR, in part, for his divorce from Betsey Cushing. FDR adored Betsey and she, him. He didn't care how much this upset James, or Eleanor or LeHand.
So, everyone, eventually got emotionally starved by FDR and had to look elsewhere. ER had great friendships but it was when FDR became governor that she fell for her bodyguard - Earl Miller - and he for her. She wrote a letter to friends at the Dem convention of 1932 saying that the minute FDR was elected she was going to run off with her bodyguard. Her despondency that FDR did not select Miller to go to Washington with them - even though he got to keep LeHand - is what drove her to the affair with Hickock. The latter relationship didn't last that long in that ER wrote Hickock "you have a feeling for me which I do not return in kind, but it doesn't mean I don't love you." ER tried batting from the other side of the plate, but it wasn't really her game.
Eleanor did continue to rendezvous with Miller in NYC and Hyde Park up until he got married in 1941, after which, he was still a fixture in her NY apt. In January of 1939 and 1940, Eleanor, her secretary Tommy, got on a plane with their respective boyfriends and flew to Florida. No kidding.
Still waters run deep. But she was starved by FDR and Miller and Hickock are probably the only two people that ever made her feel loved. No mean feat. The more you expected of FDR, the more miserable he made you. The minute you expected something in return from him as Eleanor, Lehand, etc. did, the sooner he dropped you. Look at the sulking and pouting Churchill did over Roosevelt. He and Eleanor could have had a long talk about that.
Eleanor actually enjoyed a good party and was even seen in a conga line. Esquire's 20th Century Review Women We Love issue listed ER under the category of "classy dames who secretly partied."
It's really unfortunate that the Roosevelts never got the chance to have a week without groupies and handlers to get reaquainted. They did seem oddly attached to one another and kept reaching out to the other, and missing. Sad.
The irony is, of course, the very traits that made him a lousy husband, father, etc. were the very traits that made him a good president.
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