Dear Prudence

Help! I Can’t Decide Whether to Give Up My Exciting Guy for a Better “Investment.”

Am I allowed to have my cake and eat it too?

A person shrugs, holding a devil emoji in one hand and an angel emoji in the other.
Photo illustration by Slate. Photos by Getty Images Plus.

Our advice columnists have heard it all over the years. Each Sunday, we dive into the Dear Prudie archives and share a selection of classic letters with our readers. Join Slate Plus for even more advice columns.

Dear Prudence,

I’ve gone through a lot in the last year. My now ex-husband left me after I finally got pregnant after years of trying. I decided to get an abortion, which was the hardest decision I’ve ever had to make, although I think it was the right one. I later started dating a friend of mine who’d supported me throughout the process. He’s not a conventional partner: He has a criminal history that he takes responsibility for, lives paycheck to paycheck, and is covered in tattoos, but he’s also smart, family-oriented, funny, and makes me feel excited and loved. However, we were dating long-distance, which was very hard. I got frustrated and looked for local companionship. I found a conventionally attractive man who is kind, silly, sweet. But he doesn’t excite me like my long-distance flame.

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Now it’s getting to the “DTR” conversation, and I can’t choose, even as many times as I try to do mental gymnastics. On paper (literally, I’ve made compulsive lists), my local guy would be a better “investment.” In my heart, I long for my exciting, unconventional man. Am I being selfish in trying to have my cake and eat it too? Or is this something that a grown woman must decide alone?

I don’t think dating someone you feel really excited about is “trying to have your cake and eat it too.” I think it’s just having reasonable expectations of a relationship. If you haven’t already, discussing “local companionship” with your long-distance boyfriend is a good idea, but I don’t think your dilemma is about choosing between the two of them. I think it’s a question of asking for what you want, being prepared to hear “no,” and moving on in response. Do you want to try to move to be closer to your long-term guy? Do you want him to consider moving to be closer to you? Do you want to continue dating other people in your respective towns until you can live closer? Are they OK with being nonexclusive?

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I certainly don’t recommend dumping someone you feel really strongly about in order to date someone you like less, regardless of how stable the guy’s employment or reliable his affection. You’ve been through a lot in the last year, and I don’t think you should rush into anything right now. Just be honest and upfront about what you want, what you feel, and what you’re available for. If that means eventually breaking up with both Tattoo Guy and Tattoo-Free Guy and going back on the dating market, great! (Sad, obviously, but also great.) But you don’t have to make a one-and-done decision like you’re on a dating show, picking between two suitors in the next five minutes. —Danny M. Lavery

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From: “Help! I Can’t Decide Which of the Guys I’m Dating Is a Better ‘Investment.’” (Sept. 5, 2019)

Dear Prudence,

My 14-year-old son recently came across some Polaroid pictures of me that his father took of me back when we were 14—we have been together for a long time and got married when I was pregnant with my son. The pictures were in an old shoebox filled with baseball cards and other adolescent memories. The problem is that the pictures are nude shots! You can’t really tell that the pictures are of me, as my appearance has changed pretty dramatically since I was 14—hair color change, weight difference, boobs, etc. My son came to me really worried with the concern that his father was potentially hoarding teenage porn. I didn’t directly tell him that the pictures were of me, but assured him that his father didn’t look at or keep teenage porn and that I would speak to him about it. But should I be more direct? Which is worse, thinking your father has kiddie porn or knowing that you just saw a 14-year-old version of your mother naked?

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Oh, the good old memorabilia box—it’s launched a million reassessments of one’s parents as sexual beings. You are between a rock and a hard place here. Your choices are to have your son think his father is a criminal pervert, or realize just how hot Mom was when she was 14 years old just like him! Arghhhh. (I will put aside the fact that today if two 14-year-olds—and my, you two were precocious—took dirty pictures of each other, they both could end up on a lifetime sex offender’s list.) Since your son is worried about child pornography, I think you have to tell him the truth. Get a photo of yourself, clothed, at age 14. Put it next to the dirty picture, and put a Post-it note over your nude body, just keeping your head exposed. Then show both to your son and explain he has discovered some ancient history about his mom and dad, and there’s nothing for him to worry about. Make sure all the naughty photos are put somewhere safe and inaccessible—and I don’t mean the underwear drawer. —Emily Yoffe

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From: “Help! My Son Found Nude Photos of Me as a Teenager.” (April 28, 2015)

Dear Prudence,

My husband and I have been married for five years. We have no children because I have been unable to get pregnant, even with the help of fertility treatments. We are set up with an agency to adopt, but that has also been a lengthy and emotional process, which has included a match with a birth mother who ultimately broke the match because her mother didn’t like us.

Now that my husband’s sister-in-law just had a baby, he’s more desperate than ever to start our family. He has recently told me that he is “embarrassed” by the fact that we are almost 35 and childless, and he places the blame squarely on me being “unable to produce a child.” The truth is, while I have been diagnosed with a hormonal disorder, it hasn’t been proven to be the reason why we haven’t gotten pregnant. Nonetheless, I feel ashamed and hurt by these comments. I fear I may lose my husband over this. What should I do?

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Couples’ counseling, get thee to a couples’ counselor yesterday. I know that dealing with infertility can put a strain on any relationship, and over the course of almost any marriage both parties will eventually (and inevitably) say cruel and hurtful things to one another, but framing your infertility as some sort of biological failure wherein blame can be apportioned as assigned is cruel, unnecessarily divisive, and ultimately unproductive. Be honest with your husband about how painful and unloving his words were. Make it clear that he cannot speak to you that way, especially if the two of you are planning on adopting and raising a child together—that’s no way to model familial affection for a little kid. If he can’t see the gravity of what he said, and if he’s not willing to apologize and mend his ways, then it might be time to consider parting from him, but here’s hoping he comes to his senses and tries to make things right before it’s too late. —D.L.

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From: “Help! My Husband Is Embarrassed by Our Infertility.” (Jan. 9, 2018)

Dear Prudence,

My husband of 40 years has had some E.D. The treatment is effective, but he still bought me a vibrator. As always he found a highly recommended, green, BPA-free, rechargeable one in a lovely case. The damn thing buzzes and hums so much it annoys me; I don’t require the thing, but he is like a kid with a new toy. My question is how to avoid it without avoiding him, because I really like him. The vibrator, not so much.

I’m curious if it’s this vibrator in particular that you object to or vibrators in general. If it’s the former, you can tell your well-intended husband that while you appreciate his thoughtfulness, you’d rather choose your own sex toy. (It seems only fair that if it’s going to go inside you, you should have the final say in its design, and there are plenty of gentle, nonbuzzing vibrators on the market.) If it’s the latter, you’ll have to have a slightly more in-depth conversation about your preferences. If you’d rather he get you off another way when E.D. makes penetrative sex difficult, tell him so. He sounds eager to please; I have no doubt he’ll happily comply with whatever method you’d prefer to that little green buzzkill. —D.L.

From: “Help! My Adult Son Lives at Home but Pretends We Don’t Exist.” (Jan. 12, 2016)

More Advice From Dear Prudence

I got out of a long-term relationship a few months ago, and am starting to get back on the dating scene. Not looking for anything serious at this point, just casually dating. My problem is that my ex, during an intimate moment and in a fit of frustration, once told me that I was only “OK, not great” in bed.

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