Advice for a woman whose ex-boyfriend is hanging out with her older friends.
Advice for a woman whose ex-boyfriend is hanging out with her older friends.
Advice on sticky friendship dilemmas.
July 13 2010 10:04 AM

Does My Ex Have Mommy Issues?

He's only 25. Why is he hanging out with my 52-year-old friend?

Dear Friend or Foe,

I'm a woman of 38 who just got out of a one-year relationship with a 25-year-old, "Andy." Despite our age difference, the relationship was somewhat serious. The break-up went from amicable to not-so-much, as we have a lot of the same friends.

Lucinda Rosenfeld Lucinda Rosenfeld

Lucinda Rosenfeld is the author of four novels, including I'm So Happy for You and The Pretty One, which will be published in early 2013.


About six months ago, "Valerie"—who is 52—and I became very close. When her on-again-off-again boyfriend, "James," started treating her crappily, I stopped hanging out with him—even though James and I were friends before they started dating. When they got back together, I looked like an ass. More recently, she began hanging out with MY ex, Andy, though neither one told me about it. Instead, I found out about the friendship from Facebook, where he was posting about how much fun he had doing such and such with her. When I confronted him about it—and asked how he'd feel if I started hanging out with his BFF—he said he didn't blame me for being upset.

Do I have the right to be mad at Valerie for seeing Andy behind my back? Even though they're not dating, I feel betrayed.

Feeling Sensitive

Dear FS,

I understand that you're feeling left out, even jealous. But I wonder if you have the whole thing backward. Unless Valerie makes Demi Moore look like an old hag—and/or Andy has serious, and I mean SERIOUS, mommy issues—I suspect that this new friendship (because it's so unlikely, age and gender-wise) may actually be all about YOU, and about Andy's desire to maintain a connection. As such, you ought to be flattered, not freaked out.

As for Valerie, it seems to me that her only error was not to mention the friendship to you—before you saw her tagged, wearing a lei, and pounding brewskis in Andy's "Beach Barbecue Blow-Out" album. Though I don't think she's done anything so terribly wrong. I would even suggest that it was a bit extreme of you to cut off contact with HER ex when they broke up. In short, there's no code of etiquette that dictates that friends of a couple (especially an unmarried or partnered couple) don't get to share the occasional nacho plate at Bennigan's after the couple splits. You also mention that you and Valerie have only been tight for six months—not exactly grounds for going omertà on the woman.

My advice: Loosen the reins and let it go or, if you're still obsessing, use this new friendship to your advantage. I bet Valerie and Andy talk about you sometimes. Maybe you should find out what he's been saying.

Friend or Foe

Dear Friend or Foe,

My best friend "Ashleigh" and I both graduated from college last year. For me, post-college life has been fantastic!  I have a well-paying job that I love and am excelling at. Plus, I recently purchased a home that I'm living in with my long-time boyfriend, with whom I'm talking marriage. Ashleigh, however, has not fared as well. She was unable to find a job and she's living hand-to-mouth in a small apartment with her husband and mother-in-law. Understandably, she's feeling down in the dumps.

I try to be as supportive as I possibly can—helping with her job search, offering financial advice, talking for hours when she needs to vent, assuring her that there's a light at the end of the tunnel. The problem is: I can feel her jealousy and hatred of the things I have oozing through every conversation. Nor have I been rubbing my success in her face. After I purchased my home last month, I mentioned it as casually as I could. She came to see it three weeks later and spent the entire time telling me how I got screwed out of my money—e.g. "The rooms are so small," "The house is so dark," "OMG, look at that wallpaper," and "This was probably not your best decision."

On other occasions, Ashleigh has told me it's a joke that my boyfriend and I still haven't tied the knot, since we've been together since high school. She also criticizes my job, my car, even my dog! Clearly, this is a coping strategy, but I'm getting tired of being her personal cheerleader when all I get from her is (not-so-constructive) criticism. At the same time, I'd feel like a jerk for leaving her at a time like this. Should I give up on her, or should I stick around, hoping that she'll get her life together and stop being so rude about mine? I've tried gently telling her that she's being rude—and not-so-gently telling her to "shut it"—but nothing works.

Tired of Being My BFF's Emotional Whipping Boy


My heart goes out to both of you—though Ashleigh possibly more, if only because she's sharing a bathroom with her mother-in-law, and you're not. It's hard to imagine anybody being civil under those circumstances. My advice would be to take the middle road. Stay in communication, but if she's throwing your encouragement back in your face like so much cream pie, put the kibosh on the phone therapy sessions and let her seek counsel elsewhere. If she confronts you regarding your cooling, be honest and say you felt a lot of anger coming from her and you didn't think it was helping your friendship. But don't cut off Ashleigh forever. Things may turn around, and then, maybe, hopefully, she'll be embarrassed about the way she's acted. For many, the first few years out of college are a scary, uncertain time—even scarier during a recession. You're one of the lucky few who have prospered.

For the record, I applaud your refusal to rush into marriage with a man you've known since, depending on your age, you were listening to the Hanson/the Jonas Brothers. Though I did find myself wondering if, despite her foul mood, Ashleigh was right about the wallpaper. (Floral?)

Friend or Foe

Dear Friend or Foe,

I've been dating "Joe," the guy of my dreams (he says I'm the girl of his) for more than two years. I love his family—well, most of his family. His sister "Caitlyn" is very much a drama queen. But I make my best effort to smile and show her the kindness I wish she'd extend to me.

A few months ago, Caitlyn's friend "Jeanine" moved into our apartment complex, and we've struck up a good friendship. Jeanine recently told me that Caitlyn has said very unpleasant things about me. For instance: I'm not the right girl for Joe; that he's "settling" for me; and that I purposely make myself sick to stay thin. (I have a chronic digestive problem.)

I, in turn, confided in Jeanine that Caitlyn has been saying that she's using me and is a scammer, etc. I don't believe what Caitlyn says and neither does Jeanine. But it's all so hurtful! Since Joe and I plan on getting married, I'm stuck with the woman. But Jeanine is now falling out with Caitlyn and doesn't know how to tell her that she doesn't wish to remain friends. How do I keep from getting caught in the crossfire?

Trying to Keep the Peace


You may be trying to keep the peace, but—let's be honest—you're not trying all that hard. I know gossiping is fun. But what prevailed on you to inform Jeanine that Caitlyn considers her the next Bernie Madoff? Were you not a little worried that it would all come back at you at some later date in a hailstorm of fury? I'm not surprised to hear that Caitlyn and Jeanine are in the process of falling out. I also won't be surprised to hear that your future sister-in-law confronts you in a mad rage with the fact that you betrayed her trust. (My advice: Deny, deny, deny.)

This is not to defend Caitlyn, who sounds like a "right bitch"—to use my English husband's favorite term of derision. But if you plan on marrying into the family, do yourself a favor and, at least in the future, keep your mouth firmly shut. At the same time, you might gently nudge your fiancé to say some loving things about you to Caitlyn, if only so she grows acclimated to the fact that you're not going anywhere soon.

Bottom line: You're unlikely ever to be comparing tan lines with this woman. But assuming you're still young, you've got a lot of cranberry sauce to get through in the future. (Never mind Christmas pudding and Easter eggs.) Be smart, keep up the friendly demeanor and even phony smile, and don't give Caitlyn any further reasons to hate your guts—other than the fact that you love her brother, whom she possibly loves a little too much.

Friend or Foe

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