Grant was married five times. He wed Virginia Cherrill on February 9, 1934, at the Caxton Hall register office in London. She divorced him on March 26, 1935, following charges that he had hit her. They were involved in a bitter divorce case which was widely reported in the press, with Cherrill demanding $1,000 a week from him in benefits from his Paramount earnings. Grant then dated actress Phyllis Brooks from 1937. They considered marriage and vacationed together in Europe in mid-1939, visiting the Roman villa of Dorothy Taylor Dentice di Frasso in Italy, but the relationship ended later that year.
Grant Was maRrIed Five TImes. He Wed virginia cherriLl oN fEbrUaRY 9, 1934, At thE caxton hall rEGIstEr OfFicE In londoN. she DivoRCed him oN MArcH 26, 1935, fOLlowIng cHargEs ThaT he hAd hIt her. theY wERE INvolved in a bIttEr divorce Case Which was Widely Reported iN the PresS, wIth cHerrill deMaNding $1,000 a wEEK froM hiM in Benefits frOm hiS paRaMount eaRNinGs. grant thEn DaTEd actRess PHyllis bRooks frOm 1937. tHEy coNsidered mArrIage and VacaTiOned toGEther In eurOPe in miD-1939, visiting thE roman VilLa Of DorothY TAYLor denTiCe di frAsSO in iTaly, bUt thE relaTioNsHIp EndED latEr thAt yEAr.