When ur friend asks for ur advice again ... suggest that he put himself in his gf's shoes to get the answer.....
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Clearly he isn't "madly in love with her" so maybe u can point that out to him as well...He's guilt-ridden because he's leading a double life so to speak and the only way to alieviate that ... is to stop living it.....
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Maybe his motivation for wanting to come clean isn't about feeling the need to clear his conscience but more about wanting her to break up with him...I can't imagine how he'd be able to package making a mistake 5 TIMES?....
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Infidelity is hard to handle in the best conditions, but this is a woman he works with, that he'll likely continue working with even if he stops having sex with her.....
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Not too many gfs would be able to be "trusting" in that situation.....
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What I'd suggest he do if he were asking me, is to take a long hard look at what he's doing and that, maybe, he shouldn't be in an exclusive relationship anymore...
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Angie..
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I'm the yin to Carlos'..

You could argue that it's worse for him to clear his conscience by telling her, but you could also argue that she deserves to know. You could also argue -- and, oh, what the hell, I will -- that he's not really invested in the relationship anymore, but is too much of a chicken to straightforwardly break up and break her heart. So what does he do? He breaks her heart under handedly, under the table, under the radar. As squirmy as the confession will inevitably be, he wants to tell her because he knows she'll have no choice but to kick his cheating ass to the curb. In other words, he's done this dirty deed to force her hand, to put the onus of breaking up on her. Whether or not he loves her is a moot point. He's effectively destroyed the trust of the relationship. So the right thing to do, in this instance, is for him to break up with the girlfriend. He can tell her why or not. But I think he needs to suck it up and do his own dirty work...

I don't think he wants a girlfriend. He's mid-20s. He's clearly not ready to be faithful. I think he wants to tell his girlfriend, so that it's up to her that they break up. Because it doesn't sounds like he has the balls to do it. He wants to tell her, and have her be shocked and angry and dump him. And then it won't be his fault. Timing is everything. He may really love this girl. And maybe in 10 years, he'll be ready to be true to her. But right now, he isn't. He should tell her that he wants to see other people. Because he DOES. Clearly, he does. Tell him to be a man and be honest her. He doesn't want to be just with her. He tried. He failed. Maybe later they could try again. But he needs to let her go until he's ready to be her man...