She’s not a loser but likes men who are

Q I don’t understand why my sister keeps getting involved with users. She’s 26, stunning, very creative, and extremely kind. I’m 24 and have seen her bad times with guys who take advantage of her. Our family’s considered affluent and I’ve seen right through the boyfriends who imagine a free ride with her. But she only makes a modest salary working in a fashion designer’s small business. Our father pitches in only when necessary, like when she can’t make her rent. I thought my sister learned her lesson when the last guy she dated cheated on her and then screamed that she was a spoiled brat when she confronted him. But now there’s a new loser hanging around. He never takes her out, just goes to her place at dinnertime because she’s a great cook. How can I convince her that she needs to look for someone who makes her happy instead of just leaning on her?

— Baffled Brother

A She’s lucky to have you as her brother and needs all the encouragement you can give her about her own great qualities.

You’ve described a sensitive, giving, creative woman who doesn’t yet value herself enough to be self-protective and confident in relationships.

Spend time with her in a positive way, not focusing on the past. Talking about the “losers and users” unfortunately reinforces any feelings of not being worthy of better treatment.

She’d benefit from therapy aimed at recognizing and boosting her self-worth. She’d learn that being generously giving in a relationship must work in a mutual exchange. When that doesn’t happen, it’s not her failure; it’s the wrong guy for her.

Encourage her to get therapy, even if it requires both of you talking to your father if she can’t afford it without his financial help. Explain to him (and your sister) that this is a much-needed reality check on her inner fears and self-doubts.