"I always resist falling in love," the Gossip Girl actress, 23, tells British Glamour in its December issue. "My problem is, I lose interest. Every time I've fallen in love, it's just momentary."
And Meester certainly hasn't kept in touch with any of her ex-boyfriends – in fact she would rather forget them completely.
"Honestly," she says, "I've hated every boyfriend I've had." Hopefully that doesn't include Meester's current beau, Romanian-born Sebastian Stan, who stars alongside her in the CW hit show, on which he plays Chuck Bass's rival, Carter Baizen.
On the plus side, having a heavy heart makes for great music, and Meester certainly did some soul searching while making her first record: "Somebody To Love."
"A lot of inspiration comes from my own life, because that's what I know," the actress-turned-singer says matter-of-factly. "I draw from past relationships and really sh---y ones."
Despite such unlucky-in-love status, Meester is still holding out for the real deal. "I don't want to have a boyfriend unless I want to be with him forever." But her cautious heart remains: "If I don't see an end, that's nice. Because I always see an end."