by Rudy Cheeks

Dear Dr. Lovemonkey,

My best friend has been going out with a guy for almost a year now, and it is common knowledge to just about everyone but her that this guy is sleeping around. I have seen him out with another woman (although he did not see me there). He's constantly picking up women in clubs, and he has even slept with a mutual friend. None of this has gotten back to my friend, and I have not, as yet, told her. I want to know if I should.

To some extent, I guess that it is none of my business, but there is something else that tells me that, because I am friend, I have a duty to inform her that her boyfriend is not who he claims to be. Should I tell her or shouldn't I?

-- Loyal Friend

Dear Loyal Friend,

This is one of those dilemmas -- a judgement call that crops up all the time. It would probably be the right thing to inform your friend of her boyfriend's nefarious doings, but you need to consider a couple of things first. Most important, you must be certain that your observations and suspicions are accurate and not just observations and suspicions.

What evidence do you have that this is what the boyfriend is up to? If it is merely based on gossip, it is fairly slim evidence. But, as you say, you know for sure that he has slept with a mutual "friend" (obviously not much of a friend), so that is pretty solid.

If you do decide to tell your friend, you should cut through the gossip and rumors first and discard those that you are not certain about. Then you need to tell her about the cheating of which you are certain and only that.

Next, you should be prepared to accept that this might do some damage to your relationship with your friend. There is a strong chance that she is cognizant, or at least suspicious, of her boyfriend's infidelities but has, for some reason, decided to look the other way. Indeed, if this guy is as prolific as you say, somewhere along the line the rumors and gossip have gotten back to her.

While you believe that telling her is the honorable thing and I have no doubt that you have her best interests at heart, she may see it differently and decide to blame the messenger. This is the chance you take, and you should be aware of it. Probably the best way to present the facts (and make sure they are the facts and not rehashed gossip) is to say, "Listen, I don't like your boyfriend and here is why." She may decide to dump you and keep him. Let's hope not, but it could happen.

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The following letter was received from someone who disagrees with my response to a woman who wrote to ask if it was okay to keep the ring from an engagement that was called off. Dr. Lovemonkey told her that he did not think it necessary to return the ring.

Dear Dr. Lovemonkey,

Disclosure: 1) I am a male 2) I recently did the engagement thing (successfully) 3) I will use tradition to my advantage 4) I have no personal experience with such affairs.

You really blew this one, Dr Lovemonkey. Given the amount of pressure placed on men and women who are waiting longer to get married, the amount of advertising and money involved in engagements and weddings, and the prospect of divorce, getting out of an engagement (for solid reasons) can only be commended. I think you would agree.

To suggest that a $5000 ring (or more -- let's be realistic) has the monetary equivalence of a cordless phone, tickets to Blue Man Group, pearl earrings, or a quart of Buddy Cianci's marinara (or whatever people give each other for gifts these days) boggles my financial sensibilities. To further imply that said gifts even approach the emotional equivalent of an engagement ring (even among couples who are no longer) really bothers me.

Finally, what is she going to do with it?!?! ("Oh, Suzie, is that an engagement ring?") Sell it? Wear it on her right hand to attract other potential lifemates? The money used to purchase the ring (or worse, to finance it . . . making those payments would be fun) might've been the guy's life savings (potential house down payment, school loan payoff), and she keeps it? I remain,

-- Baffled in Brookline

Dear Baffled,

My advice was that, if her former fiance asks for the ring back, to give it to him. If not, I see no reason not to keep it. You have based your argument on a number of assumptions. First, you assume that the engagement ended "for solid reasons." Next, you guess at the monetary value of the ring. Well, we know neither the value of the ring nor whether the purchase or financing of it represents a substantial amount of the man's wealth.

I do agree with you on a couple of things, though. Other gifts exchanged between the couple certainly do not approach the emotional equivalent of an engagement ring. It's emotional significance, however, cuts both ways. And, what he (or she) wishes to do with the ring is irrelevant. The ring was given as a token of a love that is now broken. It is certainly not a mere matter of dollars and cents.

Certain men of honor might take the position that it would be somewhat cheesy to ask for the ring back. While Dr. Lovemonkey has never been engaged, he has had a few meaningful intimate relationships. And when breakups have occurred, he has taken a certain posture on the post-breakup division of shared or significant items. That is that he does not contest something that his former partner desires to keep, because the value of their relationship is far greater than any mere commodity. Once again, if he asks for the ring back, I would give it to him. If not, keep it.

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