Should I let my guard down with my new bf?

A female age 30-35, *lwayznd4eva116 writes:

Hey. So I'm with this guy that I've known since about March or April. We work together and we've been good friends since we met. He's easy to talk to and a really nice guy. He's smart, funny, sweet, caring and I definetly can see myself with him in a long term relationship. The problem is, he's talked to almost every girl at our job. We use to talk seriously in the summer but I told him it wouldn't work because I was still interested in somebody else. So now, were talking again and I'm glad, but I'm having a hard time trusting him. He tells me I'm the only girl he wants and all this other stuff but how can I take him serious when the only impression he's given me, is of a PLAYER ?? I've been hurt before, and I've been played so I'm trying to avoid that from happening again. I mean I know I have to go through a lot of heartbreaks before I find the right guy, but I'm not sure if this time its worth the pain. He has a really good sense of humor, he's very sarcastic and is kinda known as the class clown at work, so I never know when he's being real with me or sarcastic. How do I know whether to let my guard down or not?

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A female reader, anonymous, writes (27 December 2009):

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