Dear Wendy: “My Friend Is Obsessed With Getting Pregnant”

It’s time again for a mega “Shortcuts Weekend.” For every question, I’ll give my advice in three sentences or less, because sometimes the answer to a person’s question is so obvious and the need to hear it so great, being as clear and frank as possible is simply the best way to go. Today we discuss pregnancy-obsessed friends, returning an antique engagement ring after divorce, and super secretive boyfriends.

I made a new friend a couple of months ago, and we have bonded very quickly and become pretty close. Fairly recently, she found out she has some health issues that make it fairly unlikely she will have children. Before she found this out, she wasn’t too interested in having kids right away. Now she is obsessed with it. Though I can understand why, I’m becoming a bit concerned. She has been taking dozens of pregnancy tests weeks before her missed period (before she could even physically be pregnant). She convinces herself that she is experiencing other symptoms of pregnancy. Although all of her pregnancy tests are clearly negative, she insists that if you look really closely, the test is positive. She just started her period and is devastated. My question for you is this: how can I be the best friend I can be to her during this? Should I try and be realistic with her, and not indulge her (by doing things like telling her I think her tests are positive, too)? Should I feed into her hope that she’s pregnant, even when I’m quite certain she’s not? So far, I’ve been sort of in between — telling her I hope she is pregnant, and either way, I’ll be here for her. But my concern for her is growing. I want to be a good friend, but I’m not sure exactly what that entails in this situation. — Concerned Friend

The best way to be a friend with her is to sit her down and tell her lovingly but firmly that you’re very concerned for her mental well-being and think she should seek professional counseling to help her process the bad news about her health. She probably won’t like what she hears and she may even stop talking to you for a while, but you’d be doing her a far better favor than playing along with her heartbreaking charade. You might even want to reach out to her husband/boyfriend, if not another close friend of hers, to “team up” in your intervention.

I am in the process of getting divorced after a two-year marriage to a man 20 years older than me. I don’t want to get into much detail, but the marriage ended on a low note per advice from our therapist who quite calmly laid out that my ex didn’t love me and was just making sure I didn’t leave because I made his life easy (I was taking care of all the expenses, working two jobs, and being a good step-mom while he spent his days checking on everything I did and downloading music). In addition, I was a great employee (I worked in his business all morning without payment, and had managed to make it a profitable business that was bankrupted when I got married).

After we separate, he’s getting a hefty amount of money as a commission for a project I developed completely, and he says he’ll only give me the divorce if I resign my share of that money. When we got married he gave me an antique engagement ring (over 100 years old) that I’m sure is worth some money, and he asked me that if he ever died I made sure that the ring got passed on to his daughters from his first marriage. I love his daughters deeply, but since I used all my savings when I was married to him by taking care of all the expenses and now need to resign the other money to be able to get a divorce, would it be wrong to sell my engagement ring? I think it’s only fair, but I feel that I’m doing something mean to his daughters. — Used Wife

I can’t speak to whether it’s legally wrong — you should talk to a lawyer about not only this question, but also helping you get the best financial outcome in your divorce. Morally, I’d say if the ring is a family heirloom, it would be the kind thing to pass it along to your step-daughters so it remains in the family. If it was simply an antique he bought specifically for you, it should remain with you guilt-free to do with whatever you please.

If you could look up “super amazing hunk” in the dictionary, you would find a shirtless centerfold of my devilishly charming, brilliant (have I mentioned sexy?) 24-year-old boyfriend of eight months opening a pickle jar. I’m absolutely gaga about him, but I’m bothered by the fact that I really don’t know anything about his life before we met because he refuses to talk about it. I do trust him, and I believe he’s the genuine, honest man he presents himself as. He’s not secretive. In fact, he’s very forthcoming about us and his future goals. There’s just this entire facet of his life that he very matter-of-factly tells me that he will not discuss. According to him, there’s nothing in it he wants to hang on to. Short of where he was born or what college he went to, I haven’t gotten word one out of him on anything else.

My family and friends all think he’s amazing, but he hasn’t introduced me to his family or friends, because he doesn’t seem to have contact with the former, if he even has any, and I know he doesn’t have the latter because he’s kind of a loner. I honestly think that if I hadn’t pursued him as hard as I did he probably wouldn’t be talking to anyone right now. I do know that he’s seeing a therapist and is on antidepressants, which he’s openly joked about. Don’t get me wrong, I’m glad he’s dealing with whatever he’s got going on — I guess it must be serious — but I sort of wish I had some idea of what that was. I really don’t want to be pushy, but he won’t even share with me basic tidbits of what he’s done or where he’s been prior to meeting me. Everything else is going really well, so should I just accept this situation or should I try to pry a bit more? — Worried Over Nothing?

Good lord, it’s not “prying” to ask your boyfriend of eight months why he refuses to introduce you to anyone in his life or tell you anything at all about his past. Don’t you watch “Mad Men”? Devilishly handsome men who refuse to open up usually have skeletons in their closet and if you want to continue with this relationship, you deserve at least a peek at them.

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