Tag Archives: May-December relationship

What It Took to Make Me Realize That I Didn’t Want to Be a Sugar Baby Anymore

Get­ting off of the ship a cou­ple of days later was a long, nerve-racking ordeal, what with pass­ports, lug­gage, and get­ting a flight back to Chicago. I couldn’t wait to be back in my own apartment—I couldn’t wait to spend some time alone and to resume work­ing. Sur­pris­ingly enough, my older man, Patrick, did not act out­raged or hurt by my flat-out refusal to get mar­ried on the cruise. We really didn’t […]

The $8,000 Mistake My Sugar Daddy Made Trying to Make Me Commit: Part 1

If sex with my older boyfriend, Patrick, was like the ele­phant in the liv­ing room, then the sub­ject of mar­riage was the dinosaur stand­ing next to it. Unlike many May-December rela­tion­ships where both peo­ple are com­fort­able just being together—or one, if not both, of them are already married—Patrick was dying to marry me. At first, it was flat­ter­ing and, although I acted pleased, I tried to make light of it, change the subject, […]

How to Bring Up Money (Or Not) In Your Age Gap Relationship

QUESTION: I just started going on age gap dat­ing web sites and I don’t know how to answer the ques­tion about what my finan­cial expec­ta­tions are. Can you help me out? CHELSEA SAYS: This is always such an awk­ward ques­tion on age gap dat­ing sites, because it assumes that you’re in it just for the finan­cial gain. While that might be true for some women, it isn’t nec­es­sar­ily the case for all May-December […]

My Rich Older Man was Amazing in Bed, But When He Did This, It Just Blew My Mind: Part 1

Being on vaca­tion with my older lover, Mr. Brown, who was also my boss, was amaz­ing and exhaust­ing. The entire time we were there, he was so atten­tive to me and my daugh­ters. Every day was beach adven­tures or trips to the zoo. At night, we went for din­ner at a fun restau­rant that catered to the kids—the enter­tain­ment kept them happy, and wore them out. We would come home at the […]