How Can I Keep My Sister Away From Her Deadbeat Lover?: Ask Harry and Louise

Our husband-and-wife team advises a woman concerned about her sister’s loser boyfriend—and about losing her sister.

By: Harry Jaffe, Louise Jaffe

Dear Harry and Louise:

My sister is in a relationship with a married man who has two kids. He keeps promising to propose to her once he divorces the first love of his life. My sister is an accomplished specialist physician, but she is somehow infatuated with this bogus character. He’s a nobody with a rap sheet of killing a man while driving under the influence of alcohol. He never told her all the complications he had in his life until he ensured that she couldn’t do without him. I have tried my very best to talk her out of it, but she seems charmed by him. Bear in mind that his real life is going on normally with his wife and kids, which makes my sister his spare-time mistress.

Please help me find a way to break them up without hurting my sister, for she entrusted me with her heart, and I can’t support her, nor can I think of a way to keep him away.

Sister’s Safekeeper

• • •

LOUISE SAYS:
I don’t like this guy any more than you do, but your sister does. There is nothing we can do about that. She is an intelligent woman who has found something with rap-sheet man that she may have never had before. She knows all the facts about the still-married chap that you do, but her feelings for him are something neither of us can comprehend. We don’t get it. Unfortunately, we don’t count. Your sister is willing to wait patiently until he’s free to marry her and attempt to forge a kind and loving life with her.

So when will it end? It will end when the horrible, gut-wrenching, guilt-laden, corrosive feelings of being with him outweigh the spirit-lifting, passionate, elated, dedicated feelings. You can’t keep him away or alter what she is experiencing with him. What you have on your side is time. Mr. Love is still married with two children. He will not be eligible for the parole of another marriage for quite a while. In this time, your sister’s feelings may begin to shift. The bad ones may begin to weigh heavier than the wonderful ones. Be there for her as a sounding board. She trusts you, and while she is not going to change her plans based on your advice, she may voice her concerns to you once the feelings shift.

If (be prepared for the big if) her feelings remain stable as she waits to become his wife, then you will have to accept him into your life. They may have a steadfast connection that no one but the two of them can understand. Shunning the promise-keeping fellow will only alienate your sister. You will have to work hard to try to shift your bad feelings.

• • •

HARRY SAYS:
Normally I would counsel someone in this predicament to butt out and let the romance live or die, but you present a very compelling case that your sister’s paramour is a scumbag, and a married one at that.

You have already tried your very best to talk her out of it. Still, she seems charmed by him. There are other, more ruthless means at your disposal. But before I suggest other ways to break up the lovers, I feel compelled to ask about your sister’s love life. Has she had many boyfriends? Has she been lucky in love? Or is she a smart, accomplished woman who needs love in her life? I ask these questions because she might be okay with being this fellow’s “spare-time mistress.” Perhaps he’s a placeholder.

If not, and you are certain your sister has hopes and expectations beyond being his mistress, then swing the wrecking ball. Expose the two-timer to his wife. You can be sly and let her know by an anonymous note; or you can be open and visit her with the unpleasant news, though that puts your relationship with your sister at risk.

That, of course, is the ultimate question: Do you feel strongly enough about your sister’s disastrous relationship to risk losing her in the process of trying to set her free?

Only you can answer that one.

• • •

LOUISE SAYS:
Slow the hell down, big shot. You and Safekeeper are acting like the lovelorn doctor is a child who still needs her hand held as she crosses the street. Your suggestion will be the catalyst that makes their lives into a compelling Lifetime movie, but it will anger the doctor to a point from which she may not return. That is, she may never forgive her sister for manipulating the situation so heavily. She’s a big girl who must steer this situation on her own.

• • •

HARRY SAYS:
If a friend, or a sister, is steering over a cliff, it’s easy to stay on the side of the road and watch her crash, say “Tsk, tsk, I told you so,” and be there to provide the soft shoulder after the damage is done. But there are times you have to take the risk of helping your friend or sister apply the brakes. It requires fortitude, which some of us have.

LOUISE SAYS (as her jaw drops):
This one is not about fortitude. She has not been kidnapped, held at gunpoint, and fallen in love with her captor. This situation is so far from ideal that it is hard to see the positive light, I agree. Sister’s heart is finding what it needs with this doozy of a character—for now. I do hope that won’t be the case six months from now.

HARRY SAYS:
Hope is not what this woman needs; she needs a firm hand, which in Louise’s case might be hard to find.