On 4 October 1590 he played cards with the king for stakes of a new "black castor hat lined with velvet". James however became angry with Lennox because he wished to marry Lilias (or Sophie) Ruthven, a daughter of William Ruthven, 1st Earl of Gowrie. James wanted him to marry a daughter of the Earl of Morton or Arbella Stewart and had Lilias Ruthven shut up in Wemyss Castle. Despite this, Lennox rescued his bride from the castle and married her the next day. After 10 days the king's rage subsided and the couple were allowed to come to court. After the death of Lilias Ruthven in May 1592, the English diplomat Robert Bowes heard that the king often received Lennox in his bed when he was away from the court and his queen Anne of Denmark.