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How can I stop my brilliant, naive sister from getting taken in by the sleazy guy who swept her off her feet?

  • Author: Wayne and Wanda
  • Updated: June 8, 2019
  • Published June 8, 2019

Dear Wayne and Wanda,

I’m worried about my sister but I don’t know what to do about it. First, my sister is special. She is in her early 20s and has always been very shy and sort of awkward with people. As far as I know, she has never had a serious boyfriend. She doesn’t even really have many friends. Growing up, she spent more time with our pets than with people. But she’s honestly brilliant, she went to a great college, and she has a fantastic job and a promising career ahead of her. We’re all incredibly proud of her, and she has a tremendously compassionate heart.

Recently, she started seeing “Jeff.” He approached her at the grocery store, of all things. Jeff is in his mid-40s, divorced, and has partial custody of his three children who are age 16 and younger. He’s handsome and all confidence and he has completely swept my sister off her feet. But I know Jeff’s ex-wife and have heard stories about how he fooled around on her, put her down all the time in front of the kids, and lied about some pretty major things. They also had money trouble.

My sister has a very good job and our family has quite a bit of money. I am certain this has played into the fact that Jeff has pursued and wooed my inexperienced sister so hard. They only started dating a month ago and he has already suggested they abandon their respective homes and buy a new place — buy, not rent, and he’s looking at places way outside his price range, of course. I have always been the big sister who looks out for her and I just know he is taking advantage of her, but I’m afraid if I say this, she’ll take offense and be hurt. What can I say or do to protect her?

Wanda says:

From one big sister to another, let me start by commiserating. It isn’t an easy job sometimes, is it? We often feel compelled to intervene with siblings when we see someone whom we truly feel to be a part of ourselves in a situation that we fear might harm them.

But your hesitation is warranted. Even if Jeff is a jerk, a user, a creepy piranha trolling for a sugar mama, your sister is now an adult — an adult who is finally experiencing the exhilarating and sometimes blinding early days of first love. Most of us experience first love — or something like it — as teenagers; at that age, we’re almost too young to truly understand the roaring complexity of it all beyond recognizing the unusual thrill of being chosen, and the buzzy excitement of those first physical connections with another.

Now imagine feeling those things for the first time not at age 14 or 15, but at 24, give or take. Your sister has enough life experience to feel this first love amplified by both her self-awareness and all the time she’s had to wait to find someone. It must feel amazing, inspiring and even relieving. There’s probably very little you can say that will dim the mesmerizing bulb that is Jeff.

Part of dating is sifting through the shape-shifting liars, the cheaters and the people who are nice enough, but simply don’t bring enough compatibility to the table. It’s hard to watch our besties and beloveds squander time with anyone but Mr. Perfect, but it’s part of the process — usually, anyway. So as much as your heart is nudging you to intervene, let it be. Trust that your brilliant sister won’t make any rash decisions, and that even if she does, she’ll be smart enough to find her way out of it, especially knowing she has a big sis she can go to for help.

Wayne says:

You can still have access to this exciting, and potentially calamitous, romantic ride that your sister’s embarking on without being all big sibling about it and telling her how to live her life. Geez!

Like many siblings, you’re also clearly her very good friend and good friends share the deets on their love lives, when they are amazing, frustrating and nonexistent. So be a friend, invite your sister to coffee or drinks, and ask her how things are going with Jeff. Don’t press. Don’t pry. Let her drive and let her spill — or not spill. If she asks for advice, give it as a friend. If she’s beaming with that new love glow, give her a big hug and tell her you’re happy for her.

If your sister’s half as smart and savvy as you say she is, she’ll know when she’s being hustled, have a feeling when things are going off the rails, and make her decisions accordingly. You might not agree with them, but that doesn’t allow you to tell her what you think she should do. It also doesn’t let you off the hook as her friend and sister. While her journey with Jeff is to be determined, you’re stuck with her for the long haul, big sis.