Posted by JenniferP
https://captainawkward.com/2025/06/16/the-return-of-the-bride-of-the-son-of-the-search-terms-the-merry-month-of-may-june/
http://captainawkward.com/?p=53021
I’ve been on hiatus to deal with some health issues and focus on book revisions due at the end of July, but I miss you all and this seems like a good way to at least visit. Let’s engage in the periodic ritual of using the search strings people typed into find this place as if they are questions. No context, all guesswork, assumptions, and snap judgments.
Here is a melancholy song with “May” in the lyrics. Sorry/you’re welcome for the earworm.
The most searched-for term is still “how to answer what are you looking for in a relationship” because people are still playing the game of trying to guess what their dates want to hear and tailor their answers accordingly, like it’s a job interview. Could we possibly break this habit?
Before you talk to this girl, get clarity about your own wants and plans. How do you see her/the relationship? Is there an “us”? Do you want there to be? Starting from right now, in a perfect world, where you have this conversation and then everything works out exactly as you hope, what does your future relationship or level of interaction with this girl look like? What, specifically, is making you feel like the air needs clearing? And why now?
Is this air-clearing talk about getting closer or about creating more distance between you?
My advice is, figure out what you want and how you feel, own your decisions, and then level with her. “I feel…” “I hope….” “Going forward, I want…”
Don’t try to sell her on agreeing that what’s best for you is the same as what’s best for her. And don’t try to draw out all her vulnerabilities before revealing any of yours, especially if this is a “we need space” conversation. Instead, be honest and forthright and give her enough information about what you want so she can decide what’s best for her.
2 “How to motivate boyfriend to take his career seriously.”
You can’t, and even if you could, you shouldn’t.
Transforming a relatively unambitious person into an ambitious one is only possible if all the people in this sentence are you. You can be as ambitious, serious, and focused as you decide to be about your own career. If you decide what you really need is a partner who matches your ambitions and career focus, then you should probably go find someone who is already more compatible.
Either way, let go of the idea that it’s your job to fix or motivate your partner to be other than what he is, and especially let go of the notion that you can influence him without his consent and active participation. Treating a fellow adult like a rehabilitation project is a recipe for misery, and it’s hard to respect someone as an equal while you’re simultaneously trying to gentle parent them into being who you really want.
Either accept your boyfriend for who he is and what he already brings to the table now, or set him free to pursue his own happiness in his own sweet time.
3 “Friend got me a nice birthday gift but I didn’t get anything for their birthday last month awkward.”
Good news: Your friend knew and accepted that you didn’t get them anything and wanted to get you something anyway. Not everyone keeps score about that stuff the same way. Your job now is to say “thank you” and enjoy the gift to the fullest. There’s nothing to apologize for or fix about what’s happened so far, though your awkward feelings might help you re-evaluate how you want to handle things going forward.
Is this an important friendship that you want to nurture? Make a note in your calendar of when their birthday is and resolve to get them a present next year. Or treat them next time you go out. “I have an extra ticket to [neat thing], be my plus one?” Or talk to them and hash out how you want things to be from now on. “I loved your present but felt bad I didn’t get you anything. Next year should we plan to swap gifts, or maybe treat ourselves to a night out since our birthdays are so close together?” Only suggest things you’d be happy to do, not things that make more chores or obligations.
If this is someone you’d rather not be on gift-giving terms with, don’t fret. Say a polite thank you for the gift now, and then keep right on not getting them a birthday gift next year.
4 “Just found out high school best friend’s mom died six months ago what to say after all this time.”
A very close family friend died this spring, and we’ve had news of several other premature and awful deaths of people we’re connected to, so this topic has been on my mind more than usual.
The best time to say something to your grieving friend is right now and the worst thing to say is nothing.
As for what to say and how to say it from a distance, death is a circumstance where postal mail comes in incredibly handy. They make greeting cards just for this, and you can write your friend a short note expressing your sympathy inside. Sample structure for the note:
“Dear friend,
I just heard about your mom, and I’m so sorry.
I still remember [how she made us pose for prom photos][ how she made us walk up and down with books on our heads to help our posture][her amazing homemade birthday cakes and bespoke Halloween costumes][her giant laugh][this very cool and useful piece of advice she once gave me][her flawless fashion sense][how kind she was to let me shadow her at her job when I had to do a presentation for Career Day][how proud she was of you at graduation][how much you loved it/hated it whenever she sent you recipes and coupons she clipped in the mail all through college][how much you always looked forward to your visits back home with her][the stories you told about her].
This note is just to say that I’m thinking of you. If you want to reach me for any reason, my current info is _____________.
With all my sympathy,
Your name
Do: Keep it focused on your friend and their mom. If you interacted with her mom, try to come up with one true memory of her like the samples in the brackets, and if you didn’t meet her, try to come up with one true thing your friend told you about her or their relationship. If you can’t say something positive you could let the greeting card industry do its “in sympathy” work for you and remember that losing a shitty caregiver is still a loss worthy of acknowledgement. There’s no pithy, perfect, idealized thing you could say that would un-complicate this for your friend, but “I’m so sorry” and “I’m thinking of you” are classics for a reason.
Do not: Say gross stuff about how the dead person is “in a better place now.” Overdo apologizing for not being in touch sooner or comment on the closeness/lack of closeness in your friendship. Marvel aloud at how long it took you to find out, especially not to guilt trip your friend about not informing you personally amid everything else they had to deal with. Make generic offers of support you have no intention of following through with. Pry into what happened. Take this opportunity to catch your friend up on all your neat life events. Make big promises about staying more in touch or getting together in the future. Expect an immediate (or any) reply.
If you weren’t actively in each other’s lives enough to learn about the death at the time it happened, then take it as a given that everybody missed some stuff about each other in the interim and that catching up can be its own entirely separate conversation.The ball’s in your friend’s court.
Doing it this way gives you the benefit of a familiar, established, recognizable structure for expressing condolences, forces brevity, and removes pressure from your friend to have to react a certain way or do anything about it. I’m not in the pay of Big Greeting Card, and I don’t know your friend, so if another communication medium works better for you, please use that. I mostly just want to help break the impasse and avoid the horrible, forced, calcified silence that so often comes after after the funeral when bereaved people and not-immediately bereaved people start to mirror each other’s internal monologues in the worst possible way:
Not-directly bereaved person: Oh nooooooo, if I don’t say something I will feel like a callous jerk, but if I bring up the loss after all this time I will remind them of their loss, put them on the spot, and make them have to talk about feelings and death, and then I will feel like an even bigger jerk. Howabout this: They can bring it up if they are comfortable doing so, but I won’t bring it up if they don’t.
Bereaved person: Oh noooooooo, if I mention death (a thing that requires no reminders when it happens near you), then I’ll make it weird and bring the whole vibe down. Nobody understands or cares about grieving people for very long, and that’s why I must hold my shit together and pretend everything is fine so I don’t make people uncomfortable..
It’s understandable to want to avoid having to perform grief or forcing someone else to perform grief, but when the “safest” course defaults to “never ever bring up or talk about grief, in case it’s awkward somehow” the end result is grieving people feeling ever more isolated.
Fuck that! Mostly I think the worst thing you can say to a grieving person is nothing. Death is awkward and there is no smooth etiquette move that cancels out the crater that’s left whenever an irreplaceable being departs from the world. Nobody’s forcing anyone to talk anything, merely inviting. So my vote is to acknowledge the loss, some way, somehow and trust that if you accidentally mess up the grieving person will steer you in the right direction. “Thanks but I’d rather not discuss it here/right now/with you.” => You can rescue the situation by saying “Of course” and then helping them change the subject. “Yeah, I would like to talk about it very much, thanks for asking.” => You can ask questions like “What was ____ like?” and then listen to the answers without judgment.
The best course is going to be highly context dependent (are you an adult, do you actually need their permission, will it fuck up your access to housing and education if they decide to play dirty, are there some legit red flags or worries here), but here are some options for *a* course of action that gives you some agency over the situation.
1. Ask your parents, one time, to share their concerns and detail their objections and commit to hearing them out. Don’t defend him or argue in the moment, even if their objections are crap. You’re not going to change their minds right now, everybody is just going to double down on their original position, and getting “emotional” or signaling noncompliance will likely be held against you. Your best bet is to listen calmly without interrupting, take notes, and promise to think about what they said. (You will think about it even if you do nothing about it, so this isn’t technically a lie.)
2. Process the substance of their objections (if any), preferably with a trusted person or people that aren’t your boyfriend. Look for patterns and themes, such as:
- Are the objections about this specific boyfriend or do they not want you to have any boyfriend at all without their permission? Is this more about objecting to him or is it about controlling you? The second thing sounds a lot like “You’re just too young, you need to focus on your studies, this is a distraction, what if you get pregnant, my house/my rules.” Controlling parents tend to be controlling about more than one thing, so if this is what’s happening it should be pretty obvious.
- If the objections are about him, are they mostly about behaviors they’ve observed or are they mostly about demographics (age, race, class & family background, money, gender, politics, religion) or physical characteristics (clothes, hair, body modifications)? Compare these sample scripts:
“He’s from a poor family and has too many tattoos and doesn’t go to our church, we want you to hold out for someone better (where better = more like us)” is not really a statement about whether he’s a good person or a good partner for you. If he treats you well and makes you happy, your happiness over time will be the ultimate evidence of whether this guy is the right partner for you. In the meantime, remind your parents that you did them the courtesy of hearing them out and now that they’ve said their piece you expect them to be courteous if they expect your attendance at family functions.
“I’ve noticed how he interrupts and talks over you, and how quiet you are/how on edge you seem whenever he’s around. He sometimes makes mean digs about your smarts or appearance, or says rude things about other people’s bodies, and while he and you insist he’s only joking, I never see you laughing. Plus, since you started dating him you’ve stopped spending time with your friends or doing things you love, and even when you try to hang out without him you’re distracted by his constant texts and keeping tabs on you the whole time. He moved the relationship along very quickly and doesn’t seem to have any friends of his own or interests besides you. I can get why that feels romantic and like you’re meant for each other, but it’s healthy for couples to have their own interests and support systems.” If your parents’ concerns sound like that, I hate to break it to you, but these are all indicators for coercive control, and your parents might be legitimately trying to protect you.
If that’s the case, what does your gut say? Do your closest and most trusted friends echo your parents’ concerns? Have you ever found yourself minimizing or hiding stuff your boyfriend does or says to you because you know your friends and parents will object on your behalf? If all the people you trust to like you hate him, that’s not a green flag. For more info, here’s an expert opinion/resource that might help.
When you’re talking about needy people, plural, it immediately suggests a pattern or multiple patterns of repeated asks where you feel pressured to give more than you’re willing to give and where you struggle to maintain consistency.
The first time you break an established pattern is usually the hardest, but once you do it new patterns become possible.The most important step isn’t finding the right words to persuade the other people to give you what you need, it’s setting boundaries with yourself to ensure your needs are met.You can’t control what other people need or when they seek you out, but you can decide what you’re willing to tolerate and control how you respond. In order to break the pattern, said response can involve words (mostly “no”) but must be backed up by actions.
For example: If a friend or relative constantly asks to borrow money, and you keep giving them the money, that establishes a pattern where it’s not unreasonable for them to assume that you’ll keep bailing them out. Even if you say words like “I hate when you ask me to borrow money” or “Please stop expecting me to bail you out” or “But this really, truly has to be the last time” or “I really can’t afford to keep giving you money like this without jeopardizing my own situation, please stop asking” but you keep giving them money, it reveals a pattern where they can expect you to hem and haw about it a bit before you give them money, but you’ll still come through. Anyone who has ever worked in fundraising knows that it’s easier to get people who have already donated to give again than to convert someone who has never donated before.
Should people believe the “soft” nos and stop asking the first time they get one? Yes, obviously. But whenever whatever should be happening doesn’t match up with what is happening, we gotta deal with what’s true. To break the pattern, you have to say “No, I can’t help you this time” and then not give them money, no matter how many times they ask, no matter how disappointed they are, and no matter what they say to try to manipulate you or how uncomfortable it gets. Their need will be whatever it is. Your consent belongs to you, and their needs don’t override that.
Nobody who has a hard time saying no got that way overnight, and undoing the habit of putting other people’s needs over your own safety, comfort, and pleasure does not disappear overnight either. Unlearning these habits are a process that can take tons of time and trial and error. Disappointing people is a skill. Skills can be learned. It might never feel good or easy, but abdicating your own needs doesn’t feel good either. Sometimes there’s no way to meet everyone’s needs at the same time, but that doesn’t mean that yours always come last.
I could (and have) write a million more words about boundaries, but this is where I want to leave off for now: The first time you break an established pattern of compliance and back it up with action, you reveal a possible world where nobody is allowed to override your consent. The more you live in that world, the more you make it real.
https://captainawkward.com/2025/06/16/the-return-of-the-bride-of-the-son-of-the-search-terms-the-merry-month-of-may-june/
http://captainawkward.com/?p=53021
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