Chelsea Handler

Comedian Chelsea Handler seems to have it all together by remaining single all these years. Not that she never dated anyone at all. But it was once reported that mega-rapper, 50 Cents, and she were linked together. Also, she did date NBC Chairman Ted Harbert.

Yes, she dates men way older than her! In one of her interviews, she claims that older men have it more together than men her age. And for her book credits, which is her own memoir, she wrote about her views about relationships and just about anything in life. Now, that’ll be a delightful read.