Dear Prudence

Help! My Best Friend Helped Me Get Over My Abusive Ex-Girlfriend. Am I in Love With Him?

Read what Prudie had to say in Part 1 of this week’s live chat.

Two sets of eyes.
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Daniel Mallory Ortberg is online weekly to chat live with readers. Here’s an edited transcript of this week’s chat. 

Daniel Mallory Ortberg: Good morning, dear hearts and gentle people; let’s chat.

Q. Bisexual or messed up? I am a 28-year-old man who has always identified as straight. Last year, I split from my long-term girlfriend, “Eva,” after realizing she was abusive. My best friend, “John,” helped me get out of this awful relationship, drove me to the hospital, and gave me a place to stay when Eva literally set fire to my apartment.

I have known John for two years, but there was an instant connection between us and we quickly became very close. John is an out gay man and I have good reason to think he has feelings for me but hasn’t acted on them because he believes I’m straight. The thing is, I’m not sure if I am, because I keep thinking about how much I want to date John. I have never felt this way about another man, but my feelings for him are strong and haven’t gone away after months of ignoring them, and I know I would have asked out an available woman by now if this were how I felt about her.

The thing holding me back is fear that I might not really be bisexual and could end up messing him around and hurting him. My sister “Lisa” is the only person I have confided in, and she is heavily skeptical of the idea I’m bisexual and thinks I’m just “messed up after Eva.” Lisa felt that I should have known way before this stage in life if I liked guys, and that if I just stop spending time with John I’ll get over this. I don’t know what to do. Should I keep this to myself and see if I get over it, like Lisa suggests, or take a risk and ask John out anyway? I’m deeply worried my sister is right, but at the same time I can’t stop thinking about John.

A: I’m not following your sister’s logic here—because you didn’t have a crush on guys “way before this stage in life” (how much sooner? Would 22 work? 15?), you’ve suddenly forgotten what friendship feels like and have mistaken ordinary gratitude for romance? What on Earth is her theory of trauma-induced bisexuality based on?

People can’t be abused out of their sexual orientations (conversion therapy comes to mind as an obvious example), and using your own abuse to discredit your self-knowledge (“You think you know how you feel, but you don’t, really, because Eva was abusive to you and now you can’t be trusted to know what you want”) is a pretty terrible thing to do. Maybe your sister is an otherwise lovely person, but she’s contorting herself into some pretty ridiculous positions in order to explain away what’s obviously true: You like John—like, like like him.

I think this is very much worth talking about with John, and leaving your sister out of it. That doesn’t mean you two have to start dating. You may not feel ready, or neither of you may want to risk the friendship: Any number of other things might possibly get in the way of a first date. And, you know, there are lots of reasons a relationship doesn’t work out; don’t feel like you’re not allowed to tell someone you have feelings for them just because you “could” end up hurting them. We could all end up hurting someone we date, because breakups are pretty common and usually at least a little painful. But you and John have known each other for two years. You trust and respect each other. He knows you’ve never dated guys before, or even had a crush on a guy before, so it’s not like you’d be withholding important information from him. Tell him how you feel and see what he has to say for himself. You can even share that you’ve been nervous about telling him because you’re relatively inexperienced when it comes to men, and you understand if he shares that concern.

Please let us know if you do talk to him about it, and keep us posted on what happens next—you sound like a lovely guy who’s been through a lot, and I wish you the best.

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Q. Makeup limits? My 14-year-old son (who is cis and gay, and has a definitely feminine style) has lately been wearing makeup. I don’t have any objections in principle, but his eye shadow is totally garish and awful to look at—think neon pink all the way to the eyebrows, à la Jem of the ‘80s cartoon. All of us adults in the family are a bit put off by it, so we decided to ask him to tone it down a notch for school. (We would ask the same of his sister if she wore her makeup like that.) Also, his grandparents are having a hard time with it, and have asked him to remove it when he goes over to their retirement community, and he has refused.

We think he should be able to wear it however he wants with his friends but needs to accept a few limits for school and some other places. I know his makeup means a lot to him, and everyone is trying to be open and accepting, but I think holding back in some times and places is reasonable. Could you please check my sanity on this? It’s all rather upsetting.

A: When I was about 14 years old, I dyed my hair bright blue with that spray-on temporary dye—you know, the kind that gives your hair the texture of straw? So I had this absolutely fried-looking electric-blue hairstyle that shot straight up. My dad walked past me in the garage (my mother forbid me from applying it in the house) and instantly doubled over laughing so hard I thought he was injured. Fourteen-year-olds are so often embarrassed by their parents that whenever the universe sends us an opportunity to reverse those roles and be embarrassed by our own children, I think we ought to think of it as a gift. That may have been the hardest I’ve ever made my father laugh.

Your kid is 14! That is absolutely prime age for exercising your (limited) autonomy and figuring out self-expression and having terrible taste. If he was being rude to his grandparents, that’d be one thing, but just because they don’t like his eye shadow doesn’t mean he needs to wash it off or apply a sedate Mary Kay shade before visiting them; they can wear as little eye shadow as they like. And it’s not like he’s going to have to scrub up for a job interview next week—I think this is definitely the kind of controlled rebellion you should treat blandly and benevolently. (The same goes for his sister; if she starts wearing super tacky clothes or makeup that she absolutely adores and that make you cringe, let her dress her heart out.) Save your energy for another battle.

Q. Not a babysitter: I made the mistake of offering to babysit my co-worker’s kids for free. She would always bellyache that she never got a night free to spend time with her husband. I was stupidly sympathetic. I volunteered to watch her kids a few times. Now she is demanding I babysit at least two times a week. Her response is borderline rude to me: “You don’t have anything else going on and we deserve a night out.” If I turn it down, she berates me and tries to weasel another night out: “Oh, Saturday you have plans. What about Sunday or Monday?”

She is aggressive and been at this company for five years; I have been here six months. She is also buddy-buddy with our manager. I feel trapped and am this close to inventing a boyfriend to get out of this. I do like her kids, but I have seen them more often than my own nephews since I started here! How do I get her off my back without making her mad at me?

A: The good news (I guess?) is that she’s already always a little mad at you, so you don’t have to worry too much about her feelings. If it’s a small office and you think she’d try to make trouble for you with your manager, I’d probably advise against being too direct—go ahead and make up that boyfriend, a weekly knitting group, or whatever other excuses you need to fake a busier schedule than the one you actually have.

But I don’t think you should give her any more details about your personal life than you already have unless you think it’s absolutely necessary; I’d stick with “I’m so sorry, I’m not available next week. Good luck finding someone!” and not elaborating further. If she’s rude enough to demand what you’re doing or tries to ask about next week, smile and act dumb: “Sorry, I’ve got to get back to work now. Good luck finding someone!” You are a smooth, featureless rock wall and she is a frustrated climber who will find no toehold on you. Be in a constant state of friendly, disinterested sympathy (“Oh, that’s too bad!” “Sorry to hear that!” “No, I’m not around that night, sorry!”), but don’t reveal anything that you’re actually up to. Once she realizes you’re no longer a reliable source of free child care, she’ll hopefully switch to being rude and aloof and you can (mostly) forget about her.

Q. Tired of being a single parent: I am a 51-year-old single parent of three. Sometimes it seems I have always been a single parent whose life has revolved around my children and has given them the best opportunities I could. I have sacrificed a lot for them with no regrets, and I wouldn’t change a thing.

The problem is my grown kids keep moving in and out of the house, or they move out but seem to always be there, or, in the case of my youngest, never move out or have the desire to do so even with gentle nudging. Not only am I dealing with that, but they treat me as if I am there to babysit for whatever or whenever they need me to do so. I love my kids and grandkids, but I am tired. I feel like it never ends, or that it has started over again with my grandkids. I don’t mind; I just would like it to be on my terms. At this point in my life, is it selfish of me to want some me time? Do I continue to sacrifice and be supportive in order for them to have the life they want?

A: It is not selfish! These are reasonable and achievable goals, and you don’t have to change the locks overnight or start behaving coldly toward your children in order to get a little distance. Start with the older ones who think of you as permanently on call for babysitting. What do you need from them? A few days’ advance notice before they ask you to babysit? A weekly limit on how often you come by to help out? Would you prefer to let them know when you’re available? If they have keys to your house, it might also be time to have a conversation about your expectations there. If you’d rather they call to ask before coming over, let them know that’s a precondition for continuing to have keys; if that doesn’t work and they’re not able to meet your request, then it might be time to (kindly, calmly) let them know you’re having the locks changed.

When it comes to your youngest (I’m assuming they’re over 18), the time for gentle hints has ended, and the time for clear deadlines has begun! (Some variation on “Your last day in the house is the ___th of _____. You’ll need to find someplace else to stay after that.”)

It might also be time to start thinking about things you want to do that don’t involve your children at all. These can be big (like planning a solo vacation) or small (taking yourself out to the movies, spending a weekend with your phone turned off and catching up on your reading). Fill your time before your children have a chance to try to claim it!

Q. Boyfriend’s family: My boyfriend has always been averse to violence. He will leave the room if a TV program has a fight scene on; he flinches if doors get slammed or if someone raises his voice.

I never put this into context until I met his family. It was like a horror movie. The “funny family stories” were his older sister describing with glee how she broke two of my boyfriend’s fingers “playing” by bending them back until they “cracked.” His brother told me he slammed my boyfriend’s head into a door until “both of them broke.” My boyfriend was 10 at the time, while his siblings were in their late teens. His parents laughed at these stories and told me what a “crybaby” their son was. It sickened me so much that I spoke without thinking. I challenged his sister and said that story wasn’t funny to me—it sounded like abuse. She told me to “get over it.” I told her that, if she wanted, I could break her fingers right now and let her see how funny she found it then. She threatened me, and I told her to go ahead—she would find me more of a challenge than a child. I stared her down and she left the room but complained to her parents. My boyfriend and I left that night. He will not talk to me about what happened, only saying that it was the “opposite of helpful.”

I don’t know what to do. I never encountered anyone in my life who acted like this, and my own family has never laid a hand on me. The big family joke was the torture of my boyfriend as a child. This was my boyfriend’s normal. I am out of my depth here. Help me, please.

A: I’m so sorry about all of this—that your boyfriend had to grow up in that family, that they’re still making light of the pain they caused him, that you had to listen to his sister crow about breaking his fingers, that in the heat of the moment you threatened his sister and put additional pressure on your boyfriend to restore the peace. While I understand and (really) sympathize with your desire to stand up to your boyfriend’s bully of a sister, it’s true that in that moment you weren’t looking to your boyfriend for guidance on how to support him. You wanted to shut her up, no matter what. While I don’t think you should apologize to her, I think it’s right to apologize to your boyfriend. Not for being angered by his family’s careless, joyful recounting of how they abused him as a child—you don’t have to try to justify that or downplay your own horror at a truly horrific situation—but for getting in a fight on his behalf and for making things worse for him. Tell him that if you had that night to do over again, you would have found a way to quietly check in with him, ask him how he was doing, and, if you absolutely needed to leave the room, make an excuse and do so without drawing unnecessary attention to yourself.

As for what comes next, while you can’t force your boyfriend to stop talking to his family or to see a therapist, I think you should certainly encourage him to find one. I also think it’s worth saying, even if it’s just once, that what his family did to him was abuse. You can make it clear that you won’t press the issue, that if he’s not comfortable discussing it with you or calling it abuse himself, you’ll respect his choice. But it’s also fair, I think, for you to spend some time asking yourself if you can reasonably expect yourself to be in the same room as his family members, at least for the near future. I hope this is just the beginning of a conversation for you and your boyfriend, and not the start of a breakup. But I hope you’re able to strike a balance between emphasizing that he gets to decide what kind of a relationship he has with his family and that you won’t try to disrupt that again, while also feeling comfortable establishing your own limits if you decide you just can’t be polite to these people—even if that means you two aren’t able to stay together.

Q. Re: Makeup limits? Consider encouraging your son to take a few classes with a makeup artist—if his current style is just too garish, it might help him get a better everyday look while also showing that you’re supportive.

A: Sure; lots of department stores and Sephora/MAC-type places offer free makeovers if you don’t want to shell out for classes, too. That’s a lovely idea, but I think the letter writer should also be prepared for her son to be provided with an example of tasteful, restrained makeup and say: “I hate this. Bring back the glitter, the spackle knife, the excessive contour.”

Q. Dating after sexual assault: I was sexually assaulted by a stranger a little over a year ago. I have gone through therapy and dealt with the trauma, but I am still not comfortable with the idea of being sexual with someone unless I know them very well and trust them. The problem is I am thinking about starting to date and don’t really know how to address my desire to go really slow. I’m also 23, and hookup culture makes taking things slow sexually seem like a lack of interest in a partner, and I obviously don’t want to bring up the reason for my discomfort early on. What is the best thing to say a few dates in if I like someone but am not ready to be physical that conveys that I’m still interested, but just need time to be comfortable being sexual?

A: First, I’ll make a plug for dating in a way that you feel comfortable with—”hookup culture” isn’t a monolith, and if you don’t want to meet too many people interested in hooking up and nothing more, I’d recommend spending more time asking friends to set you up, or using apps that prioritize longer-term relationships/pursuing people you meet during the daytime at, say, coffee shops rather than out at bars, etc. And if you’re using apps (I assume you are at least some of the time), I’d put a line or two in your profile about how you like to take your time getting to know someone and prefer to take things slow. That makes it clear that you’re not looking to have sex on the first or second date without actually coming out and saying it or offering up any unnecessarily vulnerable details too soon.

Beyond that, I think what you wrote at the end of your letter serves as a great in-person explanation. It’s not overly detailed, so you don’t risk sharing more than what you’re comfortable with, but it also makes it clear that you’re still interested: “I like you, and I want you to know I’m not ready to have sex yet. I need some time to get to know someone before I feel ready for that. I hope that’s in line with what you’re looking for.”

Q. Re: Bisexual or messed up? I think the letter writer’s bisexuality is an open question. But he is definitely “messed up,” as ANYONE would be after leaving an abusive relationship. I also think the letter writer has done something fairly natural in latching onto John, somebody who genuinely showed him loved and support at a time he desperately needed it. But that’s not a healthy basis for a relationship. Before the letter writer dates John—or anyone else, for that matter—he should take some time to work on himself and get back to an emotionally healthy place.

A: I disagree! We know the letter writer and Eva’s relationship ended close to a year ago, and that he’s subsequently spent months reflecting on his feelings for John. He’s known John for more than two years now, and they have a solid foundation of trust and mutual respect. And John came through for him during one of the most difficult periods in his life. I don’t see what’s unhealthy about that. I certainly agree the letter writer deserves to look after himself in the aftermath of an abusive relationship, but I didn’t read any signs in his letter that he’s been unstable or unpredictable since leaving Eva. He sounds like a very thoughtful, reflective person who’s been erring on the side of caution. Certainly I think he and John should talk about this carefully and not make any sudden moves, but there’s no reason not to bring the subject up—unless you see a later-in-life understanding of bisexuality as a sign of impulsiveness or untrustworthiness, which I don’t.

Q. A good problem to have? I have what most would consider a non-problem: I have too many friends! I’m a friendly, people-pleasing introvert and good listener, which makes most women I encounter in my life want to be close friends. This is primarily at work, but I also have some trouble balancing longer, pre-existing friendships. It leads to two issues: 1) no time to myself and 2) hurt feelings when I spend time or travel with someone else and don’t invite another friend who would have been interested, whether to come along or in the sense of me “selecting” another person over them. To clarify, most of these friendships have evolved separately, even if the separate friends know each other somewhat, as I am best at socializing with someone one-on-one rather than even just a group of three. I know I need to learn to say no more often. Do I need to work on making people not feel special too? How do I manage expectations when I inevitably meet new friends? I love to travel and live in different places.

Contrary to this, my romantic life has been awful and non-existent over the past five years, and I have few friendships with men. In fact, the only successful ones I have are with spouses of my female friends (of course always spending time with the couple and never with just the husband). Dates lose interest quickly, so I get discouraged. I try to adopt a mindset of not wasting my thoughts on something I can’t control, but I do desire a life partner. I’m at a loss for what I’m doing wrong on that front. I’m a 31-year-old woman, slightly overweight but conventionally attractive otherwise, independent, and intelligent. Any additional advice on remaining optimistic and becoming more confident? I have been in therapy for years to manage depression and anxiety, some of which is caused by this issue.

A: I think your second problem (having trouble dating) is caused by your first (you spend most of your free time on platonic social obligations that feel a bit forced and overwhelming). The more time you spend trying to placate various acquaintances or feeling obligated to turn a pleasant one-off interaction with a nice lady who wants to be besties into a standing weekly lunch date, the less time and energy you’re going to have for dating. If you have a lot of friends who regularly tell you they’re hurt by your decision to take a trip or see a movie with someone else, it might be worth setting aside some time in therapy to investigate why that’s a pattern for you. You certainly don’t need to go out of your way not to make people feel special, but if you notice that you tend to perform or emphasize your own empathy/curiosity when you meet new people, working overtime to draw them out and make them feel good, you can certainly try to cultivate a calmer approach, and allow yourself to make idle conversation once in a while, instead of always trying to choreograph a great first meeting for someone else.

Making a platonic connection is great! It also doesn’t always mean that you need to cultivate a friendship with every person you have a pleasant chat with and who likes you. My read here is that you sometimes approach new friendships like this: “I had a nice enough time talking to her, and she seems like a good person, and she wants to spend time with me, so I don’t have a good-enough reason not to give her what she wants.” Set the bar for new friendships higher than just “someone else wants to do it and I don’t have an objection.” Learning to say no to some of your preexisting friends will also be a challenge, since that’s not a habit you’ve previously cultivated, and I’d suggest starting small: Block out an afternoon a week, for example, where you have absolutely nothing planned and do something small and mostly-pointless simply because it pleases you. Learning to cherish and safeguard time spent alone will help you develop independence and cultivate self-confidence; later you might try to build on that by setting aside specific time for going on dates and cultivating relationships with men. I can’t promise, of course, that this will result in a life partner, but I think it will go a long way towards making you feel like your life is your own, and not a series of sexless lunch dates you owe other people.

Q. Re: Sleeping co-worker: I was absolutely thrilled to see my question published. Sadly—or maybe appropriately—my co-worker got fired for sleeping on the job too much.

A: Aw, man! I was sort of rooting for this guy. Well, I hope his next job has nap pods, and that all of your problems remain as solvable as “my co-worker is sleepy.”

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From Ask a Teacher

“I see a fair number of news stories about teachers or administrators who help out students in various ways: They give them things, go to their homes and cook or clean, and in one recent case that comes to mind, the administrator took a student to an emergency clinic. The administrator falsely represented the student as her son, and she ended up resigning. While that obviously didn’t end well, more often than not the types of stories I see are ‘feel-good’ in nature, where the student is helped and everything ends happily. My question is this: How do teachers know what boundaries to set?