Ashley Olsen, 34, And Richard Sachs, 61—28 year difference

Not to be outdone by her twin sister Mary-Kate, Ashley Olsen decidedly hooked up with a much older individual, too, in the form of financier, investment banker, and art dealer, Richard Sachs. This is clearly not the first time for Ashley Olsen to date old guy. Actually, two of her former boyfriend are over 40. Ashley and Richard was first reported by media with pictures of them riding bikes. After that, they had been spotted together for severl times.

Unfortunately, Ashley and Richard have already split up, which is rather unfortunate since they did seem kind of cute together, and were always photographed by paparazzi in their bikes, riding around the Hamptons. The reason for their split is apparently so both could focus on their separate businesses. At least that’s what their publicist says. Ashley told media that they remain friends. In any case, maybe Ashley will find someone closer to her age this time.