My Brother Just Got Engaged — Am I Allowed To Get Engaged Right After Him?

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My brother (who I am not close to) got engaged last month. I really like his fiancée! They have been together for a little less than two years, are both in their late 20s and are VERY excited to get married in October. My future sister-in-law has made it known that she wants to include everyone in the wedding planning process so no one gets their feelings hurt. I love it!

But — I want to get engaged!! My girlfriend and I (24) have been together for five years. I finally feel ready to get engaged and set a tentative summer engagement with my GF (she’s proposing, I just gave the go-ahead).

My brother’s engagement was a surprise. With how excited my future SIL is, I feel like I should wait until after their wedding to get engaged. My girlfriend does not think this matters. What should we do?

—Stressed Little Sister (Desperate For A Shiny Ring)

Dear Stressed Little Sister,

This is exactly the sort of question that’ll get me in trouble, because people have such strong feelings about overlapping engagements within families, and there’s no clear societal consensus that I can hide behind here. I even threw this question out to my high school group chat and got mixed responses. But this column is called Stephen Please, not Someone Else Please, so I’ll give my take.

I do not believe that getting engaged gives you the right to put your loved ones’ lives on pause for a year. I also do not believe that your summer engagement would take a single thing away from your brother’s wedding in October. If you were talking about proposing, say, a week before his wedding, I would tell you to pump the brakes. A buffer makes sense. Several months is plenty, in my opinion.

Unfortunately, my opinion is not really the one that matters here. If your brother and his fiancée are the type to get mad about this, you would unfortunately have to deal with the fallout of that. You can try explaining that a former twink on Substack told you it was fine, but I’m not sure how far that’ll get you. And since you have a nice relationship with your future SIL, I’d take some basic precautions to preserve it.

So here’s my actual advice: Tell your brother and his fiancée about your plans in advance. This does not need to be framed as an ask, it can just be a heads up. Hopefully, they are rational human beings who will be nothing but excited for you (and honored to be in on your secret). If they have concerns, you can still make your own decision about what to do, but at least it’ll be an informed one.

Congrats to both happy couples!

For more drawings, follow me on Instagram. Back to the advice!

What’s the right amount of pushy when trying to make a new friend as an adult?

I met “Jane” at my children’s daycare, where her child also goes. Our kids get along, and so do we! (Or so I thought.) I invited Jane and her family to a community event my family was planning on attending and, initially, she excitedly agreed. But as I tried to coordinate a time to meet, she left me on read.

A week later, I reached out to confirm our plans and she asked to reschedule. Fine by me. I put the ball in Jane’s court by telling her to let me know when they’re free. Problem is, that message has also been left on read. Not even a thumbs up.

Would it be too much for me to reach out again? I’m mostly perplexed because she mentioned she was having trouble building community, and yet, when faced with the opportunity, she turns it down, or at least communicates so poorly that I assume it’s a rejection. How do I walk the line between being friendly and annoying? Help!

I don’t see much harm in reaching out one more time. Sometimes people need a few nudges to make things happen. What the hell, give her one final nudge.

I would leave it at three attempts, though. Three’s a solid number. There’s a reason why triangles are the strongest shape, and why there are three strikes in baseball, and why you always have to give a third example when you’re listing things like I’m doing now, etc. After three attempts, the ball is indisputably in her court, and any further invitations on your part could seem pushy.

And try not to take her flakiness personally. There could be all sorts of reasons for it that have nothing to do with you — a busy schedule, social anxiety, a family crisis, etc. Maybe she’s overwhelmed right now and will come back around when she gets her head above water. In the meantime, I’d bet there are other daycare moms in need of a friend who texts back. Try to find them.

I’m currently a senior in high school and college decisions are slowly coming back this month. It’s so stressful to know that my near future is going to be decided in the next few weeks…any advice?

Here’s the perspective I can offer as a guy who graduated high school a few years ago, or maybe a little longer than that.

In the next few weeks you’re going to see some classmates get into their dream schools. Come fall, they will go, and some of them will realize they’ve made a big mistake.

And in the next few weeks, you’re going to see plenty of classmates face rejection. Come fall, they might go to their last-choice school, and many of them will have the absolute time of their lives there.

All of which is to say, the next few weeks can only tell you where, geographically, you will live in September. That is exciting, but it’s not everything. The coming weeks will not tell you how happy you’ll be, or what kinds of people you’ll meet, or what new experiences you’ll have, or how successful you’ll be post-graduation.

That stuff unfolds over years, not a few weeks. And most of it will be in your control, regardless of where you end up going. An open, curious, hungry person can make more of community college than a boring shut-in can at Yale. Where you go to college matters way less than how you go. Good luck.

And if you’ve got a problem you’d like me to solve, send it in via my anonymous form. I am no licensed professional, but hey, I am free. See you next time!