Looks like the poonhound is settling down. She's hot - a little Fiona Apple thing going on with her. Question is, will she get a gift basket when he breaks it off? http://bleacherreport.com/articles/2583563-derek-jeter-girlfriend-hannah-davis-reportedly-engaged One year after ending his remarkable 20-year baseball career, former New York Yankees shortstop Derek Jeter is taking another big step, as he and girlfriend Hannah Davis are reportedly engaged. According to the New York Daily News, the 41-year-old future Hall of Famer and his 25-year-old supermodel significant other recently agreed to tie the knot. While an official wedding date has yet to be released, a source reportedly revealed to the New York Daily News that The Captain has already presented Davis with an engagement ring. No. 2 was well-known for his dating exploits over the course of his baseball career, as he was linked to the likes of Jordana Brewster, Adriana Lima, Jessica Alba, Jessica Biel, Minka Kelly and Mariah Carey, among others, per Brendan Kuty of NJ.com.