I keep telling my girlfriend she’s attractive but she isn’t.

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Photo illustration by Slate. Photo by iStock.

Mallory Ortberg
Mallory Ortberg

Sam Breach

Mallory Ortberg, aka Dear Prudence, is online weekly to chat live with readers. An edited transcript of the chat is below. (Sign up below to get Dear Prudence delivered to your inbox each week. Read Prudie’s Slate columns here. Send questions to Prudence at prudence@slate.com.)

Readers! Ask me your questions on the voicemail of the Dear Prudence podcast. Just leave a message at 401-371-DEAR (3327), and you may hear your question answered on a future episode of the show.

Q. False compliments: I give a lot of positive feedback, compliments, and advice to family, friends, and my girlfriend. I’m considered a very positive person and was once told by my girlfriend that I was great for her ego and self-esteem. She has struggled with her confidence in the past because she is very skinny. Before we became a couple, I constantly complimented her on how beautiful she looks to lift her spirits. The problem is that I am more in love with who she is internally (she is smart, funny, caring, loving, and super supportive) and not particularly attracted to her externally—but she would never know that based on my many compliments.

I feel so horrible lying to her about her beauty, but I can’t fathom breaking her heart and self-esteem in the process. Please help.

A: I am not sure why you got into a relationship with a person you are not attracted to, but if you’re happy with your situation, then I suppose I’ll leave that aside for the moment. Are you telling your girlfriend kind things that you believe to be true about her appearance, even though they’re not backed up by a powerful personal attraction on your part? (You can not be attracted to her and still think her hair looks great today or that she has a lovely smile; it’s not a lie to compliment something without finding the person you’re complimenting attractive.) Or are you saying things you yourself do not believe in order to “boost” her self-esteem? If it’s the latter—that sounds awful, and my advice to you is to spend some time in therapy exploring why you’ve sought out a woman whose greatest fear is that she is not attractive and pursued a relationship with her knowing that you were, in fact, her greatest fear realized. You say you’re “considered a very positive person,” but there’s nothing positive about bombarding someone with insincere flattery if it’s not genuinely meant.

Let me add that I don’t think you should share any of this with your girlfriend, as it would be unnecessarily cruel. This is something that should be shared in confidence with your therapist. Whether or not you’re able to see your way through to a continued relationship, none of the information you’ve shared here could ever be helpful to her. It could only hurt.

Q. Bad timing: “April” and I grew up together. Our parents are best friends, so she has always been a fixture in my life. She is three years younger than me. April came out when she was 15. I didn’t figure out I was gay until I was midway through college. My problem is now I realize that I have fallen pretty hard for April.

She is the first person I think about when I want to share good or bad news. She’s kind, clever, and cute. I think I had feelings for her for a long time but pushed it off as her being “only a kid.” April is dating someone right now. It is new, but she made a point to introduce her to everyone as her girlfriend. But April’s older sister also told me how glad she is that April got over me! Apparently April has had a crush on me since “forever,” and I never noticed.

I don’t know what to do with this. I feel completely stupid for missing this. Part of me just wants to confess openly to April, but I don’t want to hurt her or mess up our friendship. I can’t turn to anyone in my family because I am terrified it will get back to April. Should I just sit on my feelings?

A: You have more options for sharing your feelings than just “tell your family members who consider April a relative” or “say nothing, forever.” You can discuss this with other friends who aren’t as close to the situation and ask for perspective and advice. If your goal is to make sure you don’t make April uncomfortable or damage the friendship you already have with her, then I think for now the best choice is to say nothing. You’re both young, and the odds that she will be with her current girlfriend for the rest of her life are fairly slim, although I don’t think you should put your own life on hold indefinitely in the hopes that she’ll be single again.

If, after talking it over and considering your own feelings, you decide you want to say something, then it’s best to do so with the understanding that you’re taking a considerable risk and that she may no longer feel the same way or cares for her new girlfriend too much to end things and try a relationship with you. If that’s not a risk you’re willing to take, then don’t do it.

Q. Do I have dementia?: I am a semiretired professional in a high-tech field, and my services are in demand. I work from home. Other demands on my time are housekeeping (I only do as much as I want, because we have help and money) and babysitting—my husband and I have two lovely grandchildren. My problem is my husband, a former teacher who does not do any professional work (the kids and I try to keep him occupied with tasks like online shopping and house renovation; he does not seem too interested in other things). He hovers over me, watching over everything I do and frequently commenting on what I should do.

This makes me nervous. If I am on my own, such as on business trips, I cope. This makes the trips a real holiday for me. I am 64, and I do have some risk factors for dementia. I love my husband—we have been together since our teens. So I am wondering whether he thinks I need supervision, or whether he is bored or has some power issues. Currently, I am considering an appointment with a dementia specialist. Do you have any other ideas? For what it’s worth, when we had other issues, he refused counseling.

A: I think it’s always a good idea to check in with a doctor if you’re concerned about risk factors for a medical condition, but you don’t say you’ve started forgetting things or experiencing confusion. I wonder if you’re experiencing retired husband syndrome—now that he’s not working, he finds himself at loose ends and isn’t quite sure of what to do with himself, and he’s looking to you to entertain and occupy him.

Just because he hasn’t wanted to go to counseling in the past doesn’t mean you can’t speak up if something’s bothering you. Tell him you’ve noticed his recent hovering, and it’s made you anxious that he thinks you need supervision or might be developing signs of early onset dementia. If he says, “No, I just like spending time with you,” you can say, “Great! Watching me work and offering me advice is not fun for me, so let’s find some time after I’m finished to take a walk or talk or share a cup of tea.” You can set limits with him—but you do have to speak up and say something. You don’t have to let him be your constant shadow.

Q. It’s not you, it just is?: I want to break up with my boyfriend. I mean, technically I have broken up with him. He’s my ex. It’s just that he insists I have to have a reason—“Is there someone else?” “Was it what I did?”—and if I don’t then we aren’t really broken up.

We come from a small town and have a close-knit group of friends who also want to know why. So do I just make something up? Or throw a fit until people stop?

My reason is basically apathy. He texted me to go out one night, and I realized I’d rather stay home and watch reality TV. And that was how I felt about him: He’s a nice guy, but I have less emotional investment in him than in any of my hobbies. We’ve only been going out for a couple of months.

A: To him: “I broke up with you because I didn’t want to keep dating you.” To others: “I broke up with him because I didn’t want to keep dating him.” You do not need to convince him that you have a good-enough reason to break up. If he keeps pressing, feel free to hang up the phone, walk away, or otherwise end the conversation. His current behavior is only further justifying the choice you made to end your relationship.

Q. Not forgetting: My mother was a free spirit. While she was married to my father, she spent a lot of time on solo adventures, one of which ended with her pregnant by another man. My father took me to where my grandparents lived and divorced her. I never saw her at all. She never contacted me. I grew up and went looking for some answers. My mother married the man she had the affair with and had four other children. The younger ones didn’t even know I existed. I never got an apology from her, only a lot of excuses and crocodile tears.

I honestly don’t want anything to do with her or her husband (he tried to blame my father). But I am interested in building a relationship with my half-siblings. “Amy” is in college and closest to me in age. We talk a lot and have even gone on some trips together. Amy keeps trying to get me forgive our mother so we can start “being a family again.” She doesn’t understand why I carry a grudge. My mother left my father and me as soon as she could upgrade to a better model of family. For 20 years, she ignored me, didn’t fight for me, or pay one red penny of child support. I don’t wish harm on her, but I have no interest in letting bygones be bygones.

How do I keep my relationships with my siblings separate and get Amy to understand? My pain isn’t their fault, but Amy keeps pressing on the wound.

A: “She’s not a part of my life, and I don’t consider her to be my mother. I understand that your relationship with her has looked dramatically different from mine, and that you may wish things were otherwise between us, but I’m asking you to respect this and to stop asking me when I’m going to forgive her and let her back into my life. She’s never been in it. I’ve loved getting to know you, and I value our relationship, so I very much hope you can respect this request.”

Q. Wedding witch: My half-sister has rescheduled her wedding three times as of this year, including canceling it once because her fiancée cheated on her. Now her new date is smack dab in the middle of my planned trip to Australia to see some of my oldest and dearest friends.

I have planned this for more than two years and have put down thousands of dollars toward this trip. My sister told me told me I had to cancel and be there for her special day. I told her I would have been happy to come for any other day but I couldn’t come on this day and I was sorry. She threw a hissy fit and told me I was “ruining her wedding.” She has repeated this line of thought to everyone in our family, and I am sick of it. How do I deal with this?

A: Let her be as unreasonably angry as she wants, and go on your trip. Have a great vacation!

Q. Ex-husband’s stepdaughter wants to follow me on Instagram: I have been divorced since 2013; my ex and I don’t have a good relationship, and I have no relationship at all with his new wife. I reached out to her when I knew that she would be the stepmother of my three kids but never got a response. Over the weekend, her 13-year-old daughter requested to follow me on Instagram. My son and I interact on the platform and that must have been where she found me. She and I have been in the same room before but have never been introduced.

I plan to ignore the request, but my question is this: Should I let her mom know that her daughter is requesting to follow adults she doesn’t know? If the situation were reversed, I would want to know, but I don’t want to make an already uncomfortable situation worse. I would hate for her to think that I am judging her parenting choices, for example. What do you think I should do?

A: I think it’s right not to accept the request, but I don’t think it merits a follow-up with her parents, given that you know that she knows who you are. This is not the same thing as sending follow requests to adult strangers; this is a display of the natural inquisitiveness of a teenager who knows you’re in some remote way a part of her family. Ignore the request and leave it alone.

Q. Re: Bad timing: Tell her how you feel. Tell her, tell her, tell her. April is the only person who can decide if she has moved on or not. Maybe she has and will have no issues remaining friends. Maybe she has moved on because she thought she had no other choice but to. The point is that the letter writer will never know unless she has an open, honest conversation with April.

She isn’t married, and it sounds like she is in a fairly new relationship. Better to have this conversation now than once she is in a serious relationship—or married. You know this conversation will happen at some point.

A: That’s at least one vote for speaking up now! I’m inclined to be slightly more risk-averse, I think, but you’re right that this relationship is fairly new, and the letter writer isn’t contemplating an affair—she’s contemplating offering information that April doesn’t have and that might influence her romantic choices, if she had it.

Q. Brother won’t let dad meet his baby: Despite having been raised in different parts of the country, I have developed a wonderful relationship with my older half-brother, “Tony,” over the last few years. When he was an adolescent, our father made the painful decision to cut off contact with him because of the strain it put on his relationship with my mother. My father is a wonderfully caring man, is regretful about how he treated Tony, and has reached out a number of times, including recently when Tony’s daughter was born. Tony refuses to acknowledge these efforts.

While I understand that Tony doesn’t have the same insight into our father’s choices as I do, I feel that he is being punitive and small by refusing any type of rapprochement. My father is dying to meet his first grandchild, but I can’t even mention our father to Tony without him making a face and changing the subject. How can I talk about this with him?

A: Earlier I answered a letter from someone else who’s in Tony’s exact position, and I’m going to give you the exact same advice in reverse. You cannot, and should not, try to manage your brother’s relationship with your father.

Just because your father was caring toward you does not mean that he is incapable of doing the wrong thing, and by your own account, he chose not to be a parent to your brother. Whether or not you think he had sufficient reason to abandon his own son, and whether or not you think his current regret outweighs his past choices, is frankly irrelevant. Please respect Tony’s decision and let him choose whether he wants to re-engage with your father. You cannot pressure him into forgiveness, and you should not attempt to do so. Your goal should not be to “talk about this” with Tony (by which you mean, “convince Tony to see things the way you do”). Your goal should be to let him make his own decisions and to respect the boundary he has so clearly drawn.

Mallory Ortberg: Thanks for joining in, everyone. Remember, Slugworth would give his front teeth to enter the inventing room—give him nothing.



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