My Little Sister Got Engaged Before Me: Here’s How I’m Navigating This

This post is all about how I’m feeling now that my little sister got engaged before me!

My little sister got engaged before me.

Let me start by saying that how I feel now isn’t totally how I felt in the beginning, though I wish it was.

But before I dive into the specifics, here’s some background on my relationship.

My boyfriend David and I started dating in 2018. 

I lived in Raleigh, NC at the time, and he lived in Jacksonville Beach, Florida (about a 7 hour drive). After dating for about 8 months, we decided we were over the long distance and it was time to move closer to each other.

I wasn’t ready to upend my career and move that far away from my family in Virginia, so David ended up quitting his job and moving up to Raleigh.

We lived in Raleigh together for about three years before deciding that we’d probably be much happier at the beach. So, we ended up moving back down to Jacksonville Beach together.

At this point, we’d been dating for about 4ish years.

Fast forward two years in Jacksonville Beach and we’ve now been together for almost 6 years. 

When I think about 6 years, I’m a little mind blown. It doesn’t really feel like we’ve been together that long, but then again when I think about all of the things we’ve done (and overcome) together, of course it makes sense.

So now we get to the fact that David and I are both 30 years old and we are not (yet?) engaged. So let’s dive into all the nitty gritty details. I’ll start by answering some of the questions that I am commonly asked.

Prepare yourself for some rambling 🙂

Two people holding hands with an engagement ring.

Do You Even Want To Get Married?

My answer is a resounding yes, for sure. But I don’t really have any desire to plan a wedding. And candidly, I have no desire to spend $30k on a day that would likely make me more anxious and miserable than happy. (I’m a pretty anxious person and can just see that happening to me). But I do want to have some sort of wedding. I do want to walk down an aisle in a pretty dress. I do want to celebrate with my family and closest friends.

I also really want to have children, and I’m frustratingly aware of the timeline that my body has when it comes to its ability to bear children. How could I not be?

I don’t really want children at this very moment, but I do think about how the window is getting smaller all the time. I also think about our parents, or our future child’s grandparents. Not only are we growing older which would make us older parents but that would also make our parents – our child’s grandparents – older, too. 

And I loved my grandparents. So I want my children to be able to spend lots of time with theirs.

I also think about how happy I am in this stage of my life. We love our weekends where we wake up, light a candle, brew a pot of coffee, watch whatever on our Roku on the couch with our 3 year old chocolate lab, Bogey.

It sounds so simple but we both love it so much. And not that an engagement would change that, but… it does mean the next steps of life are well on their way and what if I just don’t even want to burden my mind with those things yet?

Two people about to kiss and smiling.

Have You Two Talked About Getting Married?

Yes, plenty of times. Unfortunately, a few of the conversations were sparked due to people in my life asking me where we we’re at or “what’s David thinking?” and then me not being 100% sure, and then me getting worried, and then bringing it up to David while I’m in a state of worry, and then the conversations aren’t so great or productive.

But when I block out the outside noise, ask myself how I’m really feeling about the situation, and then talk to David about it all, the conversations are much more productive and true to us.

You know at the top of this post where I said “how I feel now isn’t totally how I felt in the beginning” ? What I meant by that was… I used to get really worked up when I wasn’t really sure where David and I stood. Marriage and engagement have always felt so BIG to us, so we weren’t ever the kind of people who talked about it nonchalantly. But then, when a concerned family member asked what the plan was, it amplified my own uncertainty and threw me into a tailspin. As if for some reason whenever I shrugged my shoulders and said “I don’t really know!”, that answer never felt good enough judging by the looks on the faces of those that asked me.

I’d be lying if I said I didn’t freak out on David a few times. Like… what’s going on!? I’m getting old (lol) and we’ve been dating for 45 million years and idk where your head’s at and AHHHHHHHHHH.

And sometimes, I still find my thoughts creeping in that direction. But I do my best to trust that David will propose when he is ready to, but more importantly, when he feels it is right for US.

Sometimes, this is very hard. Especially as someone who likes to be in control of her life as much as she possibly can be. This is certainly one thing that I do not have complete control over. Maybe this’ll be good for me LOL.

I also don’t want to eventually be proposed to and instead of feeling excitement and “YAY this is awesome, I get to spend the rest of my life with him!!” I feel overcome with relief because I’ve been waiting on pins and needles.

I don’t want relief to be my number one emotion on that day. I just want to feel joy. And so, I believe that in order to feel joy on that day, I have to trust that things will work out, and not spend my days worrying when? when? when?

If you’re in a similar situation to me, then I’m sure you can relate when I say that these are big life decisions that you’re likely experiencing for the first time. And even if it’s not the first time – it’s still a convo about a decision that to us, anyway, means forever. And the older you get and the more unpredictable (and tough) you realize life is, the more weight a decision like this can hold.

I’ve actually thanked David a bunch of times for not proposing to me yet, too. Like I said before, I really like how our life is right now.

Two people sitting next to each other on a bench in the city.

What Was Your Little Sister’s Engagement Like? 

I wrote a bit about this in one of my captions recently but when I first heard that my little sister Katie was getting engaged, I was ecstatic for her, and felt a little weird for myself.

I called a couple people I’m close with. Told them. They were happy for my sister of course, but unsure how to react when it came to me.

It’s like we all were trying to figure out if we should feel sorry for me. Should I feel sorry for myself? Should I be embarrassed? This is embarrassing… right? Society says if your little sister gets engaged before you that this is embarrassing! So… based on that logic… I’m embarrassed! Everyone, please feel sorry for meeeeeeee! 

And I rode that logic for a day or two, maybe. Then I thought… wait a second here… why am I embarrassed? Because society says I should be… okay… but society aside, do I feel embarrassed? No? Well then, let’s go with that feeling instead.

That’s the key to all of this, I think… throwing away the thoughts and opinions of society and even the people who love you the most and asking YOURSELF how you feel.

It’s okay to feel happy for your sister and a little sad or worried for you. But I hope if you do feel a little down it’s because you want a little more clarity on if or when your person will propose to you (relatable), and not because society says you should be embarrassed. F that.

As for her engagement – it was awesome. I cried because I was so happy for her. Seeing someone you love feel so loved is such a beautiful thing.

I love my sister more than anything. I just want her to be happy. That is all that I care about.

Ultimately, my little sister getting engaged before me has absolutely nothing to do with me. If she and her person want to move on to the next steps of life together, they shouldn’t wait until I do so first… they have to do what’s best for them. I wouldn’t want them to do otherwise.

Two people getting engaged on a mountain top.

When People Ask About You Getting Engaged, Does It Feel Triggering?

It only ever felt triggering when I was unsure. It was almost like, the more people brought it up, the more I would think “wait, yeah… I guess we are behind aren’t we? I guess I should know more, shouldn’t I?”. If I was in that headspace and someone asked me, that’s when I would get a little frazzled internally.

But when I’m in a good headspace, and people make comments, I don’t care. I even think it’s funny! And I really don’t fault people for being curious either. I do it, too. If people have been dating for a couple years I’m always curious if they want to marry each other. But now that I type that out and read it over… it’s a little bit cringey. Why are we so curious about people’s most personal relationship that they have? It’s really none of our business… 

I’m honestly happy, though, that I’ve had the experience of my little sister getting engaged before me. I’m always oddly grateful when different things happen to me (like when I got laid off in Paris) because once I navigate it, I can help people who go through a similar experience down the line. And I love that!

So anyway, the short answer to this question is… I haven’t been triggered by someone asking me about it in a while (thank goodness) but yes, I’ve absolutely experienced it before and it doesn’t feel good. If you’re in a similar situation now, maybe you could talk to your person and get a little more clarity for your sanity. If that’s too difficult right now, at least know that there is no set timeline and that you are absolutely not alone in your feelings!

Two people kissing in the ocean.

How Are You Doing These Days?

These days I’m happy! I love the life that we are building together. One day, I hope we get engaged, but if it doesn’t happen for a little while, that’s okay, too.

There will always be people who have an opinion or a judgment. But at the end of the day, as long as I am okay with how my relationship is unfolding, that’s all that matters, ya know?

Wishing you the best with your situation, too. I truly believe it always works itself out.



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About Taylor

A few years after graduating college, Taylor made it her mission to become debt free. After paying off all $60k of debt, she began to blog about what she's really passionate about: personal development. Nowadays, Taylor blogs about the topics of Mindset, Money, Health, and Career for women.

"It's Per$onal" is a super popular and anonymous blog series about the personal lives and finances of women all over the world. Check it out!

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