Should I ask a guy to the prom? I am a girl and and I want to go with this one guy, but I feel like he may be too shy to ask me. But I am not sure if I should be the one doing the asking. —Jenna, 18

As the great Steven Patrick Morrissey once crooned, “Shyness is nice, and shyness can stop you from doing all the things in life you’d like to.” So, yes! You should totally ask this dude to the prom! Though it seems like you’re more worried about tending to the archaic tradition of THE MAN needing to be the one to ask. If that’s the case, ain’t no thang, my boo! This is 2013. Girls can totally ask guys out, and if that’s not gospel by now, let’s do our part in spreading it. Plus, if he is shy, then you’re totally doing him a favor, and how nice of you to take the pressure off of him. Now: if he says no, please don’t stress about it or feel embarrassed. You went after what you wanted, which is what you should be doing, and he didn’t say no because you asked. And there are other prom dates out there. Go for it, so we can focus on more-important things, like what you’re gonna wear. —Marie

My brother has a new girlfriend, and I hate her SO MUCH. He’s two years older than I am, and we’ve always been close, but ever since he started dating this girl, it’s been different. They spend all of their free time together, so I never get a break from her. She’s got a really loud and insincere laugh, and she demands attention from everyone all the time. I can no longer have a conversation with my brother without her interrupting. My brother is such a nice and loving person, and I think she’s taking advantage of him. Obviously, I’m happy that he’s happy, but I think he’ll end up sacrificing things he wants to do to please her. What do I do? —Anna

Something people don’t talk about enough when it comes to other people’s relationships is how it feels when someone you love and care about deeply (in a platonic or familial way) starts dating someone you don’t even like. It’s a weird spot to be in, because common sense pretty much dictates that we shouldn’t meddle in other people’s relationships. On the other hand, sometimes you just wanna be like, YO, IS THIS FOR REAL? There have been so many times when I have wanted to tell one of my friends: HE IS BENEATH YOU IN EVERY WAY AND HIS JOKES ARE NEVER FUNNY. DUMP HIM AND GO BACK TO BEING AVAILABLE TO ME WHENEVER I WANNA HANG BECAUSE I AM YOUR BEST FRIEND.

Let’s break it down. There are two main issues here. The first is that you don’t like her. The second is that you feel like you are losing your brother, and you miss the closeness you shared before she came along. Unfortunately, there isn’t a lot you can do about the first problem. You might not get along with her, or you may think she’s fake and not good enough for your bother, but we have to accept the people our loved ones choose to love. You probably feel like you know her from your interactions with her, and what you know of her may seem absolutely heinous, but that doesn’t mean you know her the way your brother knows her. She might be kind and compassionate and necessary to him in ways that are private and only understood by them. Then again, she may be a superficial, narcissistic jerk. Regardless, the only people who really know what goes on within a couple are the people in the relationship. You’re not going to convince your brother to turn on her—he has to come to that conclusion on his own, if ever. In my experience, broaching the subject can only backfire and possibly cause him to resent you for disrespecting his girlfriend. The plus side? If she’s as awful as you say, he might start to see this for himself after the newness of the relationship fades, and if and when he does, he might come to you for advice or just to vent. And then perhaps you could gently and tactfully let him know what you think of her.

When people start dating someone new there is always that period of euphoria where you feel so enamored with the other person that you want to spend all your time together for days or weeks on end. It’s wonderful and all-consuming, and it’s only fair that you let him experience it—at least for a little while. However, it’s also more than fair of you to remind him that you are someone who loves him and values him and misses hanging out with him. Healthy romantic relationships do not come at the expense of all other existing relationships, and you should remind your brother of that little truth nugget. Tell him that you’re glad he’s dating someone he’s into, but you also miss him and it’s not the same when his girlfriend is around. Suggest a time when the two of you could hang out without her. I predict that he’ll understand, and be grateful that he has such a loving, thoughtful sister. —Jenny

I have a friend who is very dedicated to her band. Music is her whole life, and I’m really proud of her for following her dream, but the problem is that whenever we make plans, she cancels on me at the last minute because she forgot she has band practice or is recording or something. I get so excited when I think we’re going to hang out, and then feel so crushed when she bails. How do I tell her how much stress she gives me without sounding needy or unsupportive? Confrontation is not my strong suit. —Allison, New Jersey

It doesn’t matter if your friend is in Beyoncé’s all-lady band or whether she is following her dream of eating piles of Hot Cheetos while watching a marathon of Ask This Old House—she is being a bad friend. Yes, being in a band can be really thrilling, and also all-consuming: it takes a lot of dedication and hard work, especially in the beginning when you’re trying to get it off the ground, and it’s probably making her a bit blind to the world as it exists outside of her practice space. Chances are if she’s ignoring you she’s ignoring all of her friends, so don’t take it personally. Still, you are not being unsupportive by mentioning this to her—you are asking your friend to respect your time and honor your friendship. From my experience in bands, rarely is there a sudden or surprise practice. These things are generally regimented and scheduled, because that’s what it takes to get a couple of people in the same place at the same time every week. It sounds like your friend might just have trouble organizing and planning in advance, and also perhaps like she’s taking your availability for granted.

I would start by making a morning plan. It’s very unlikely there will be a band function before noon, so there is no reason for her to flake, and this way you can have a face-to-face chat about what’s going on. Tell her that you’re really psyched to finally hang out, but that you’re bummed that she frequently cancels at the last minute. You can let her know that you understand how much the band means to her, but that it still hurts your feelings. Keep it simple and be direct. You can also ask what her schedule is like and when it’s best for her to meet up so that you have a better idea of when she’s available. But the main thing here is not for you to work around her ambitions and labyrinthine schedule, but rather for her to understand the consequences of her behavior so that she has an opportunity to change and be more dependable in the future. Good luck. —Jessica

I’ve been with this guy for two years, and the relationship is starting to bore me. I like to go out and do things every once in a while, but he wants to stay in every night. Like on Valentine’s Day, I wanted to go out for burgers, but he refused and just played video games all night. Do all relationships become this monotonous after a while, or is it time to start thinking about breaking up with him? —Sam, California

Unfortunately, your relationship does sound like it’s in a rut. I’m sorry, but it can happen to the best of us. To answer the first part of your question: no, not all long-term relationships become that monotonous, but it is a struggle to find a balance between being comfortable enough with each other that you can be yourselves, and being so comfortable that you stop trying to impress each other.

Before you break up with this guy, give him a chance. He could be completely unaware that you’re feeling so bored and unhappy. The next time you’re hanging out at home, sit him down and let him know that you’re disappointed with the current state of your relationship. You don’t want to do this in the middle of a fight, because then you’ll both be defensive. Also, even if you think he’s responsible here, I wouldn’t begin by blaming him. It would be more constructive to tell him all the things that you appreciated about him when you first got together, and ask him to tell you the same in return. Explain that you’d like for both of you to value each other’s company and work a bit harder to make each other happy. And then it’s time for you both to commit to some changes.

Here’s the tricky part: getting excitement back in your relationship isn’t just about going out for expensive dinners. Remember when you first got to know each other and just making a sandwich together was fun? Relationships exist at all times, not just when we’re at theme parks or during nighttime strolls on the beach. You need to find new ways to enjoy each other’s company. Do you like video games? If you’re interested, ask him to play with you or to teach you a game. Rent a movie that you both want to see and eat dinner while watching it. Share YouTube videos that made you laugh. If you’re having sex, do it in a new place. If he likes to stay in and you like to go out, compromise: ask him to plan something for you both to do at home on Friday, and then you can organize a fun night out on Saturday. Mix up your routines, and I mean all of them. Take a different route to go to the movies, and if you go to the movies a lot, go to Toys “R” Us instead. It’s an exercise in breaking old patterns and embracing new things. The goal here is to let go of the resentment you feel towards him and see him with fresh eyes, so you can remember all the reasons that you started liking the guy in the first place.

But this is all dependent on whether he wants to make things exciting again. If you bring this up and he balks or condescends to you? Then, my friend, it’s time to rethink the relationship. Your happiness should be important to him, and if he’s not interested in making you feel special and spending time with you in a meaningful way after only two years, it’s not likely to improve with time. —Emily G. ♦

If you have a question for next month’s Just Wondering, please send it to [email protected].