We wrote this about a real Reddit thread with actual comments shared by readers in the wedding planning community.
You have spent your whole life navigating the twin thing. The constant comparisons. The people who skip one birthday party because they already went to the other one. The relatives who have said, out loud, which one is the pretty one and which one is the smart one. You know how this goes.
Now your sister's boyfriend is probably proposing soon, and you and your partner are also talking about marriage. You want her to have a wedding that is fully hers. You want the same for yourself. And you are trying to figure out how to make that happen without pushing your own timeline to 2029.
You do not have to wait that long. Here is what people who have actually been through this say.
The consensus: three to six months between weddings is enough
Several twins responded to this thread directly. One pair got engaged within a week of each other and married three months apart. Another got married in May and October of the same year. A triplet got engaged seven weeks before her sister and married three months ahead of her. None of them reported disaster.
The couples with the most friction were the ones who had large numbers of out-of-town guests who had to choose between two travel expenses in the same year. That is the practical issue worth planning around: not whether you can be engaged at the same time (you absolutely can), but whether your shared guest list can realistically attend both weddings without financial strain.
If most of your guests are local, three months of separation is comfortable. If many are flying in, you may want five or six months, or even different calendar years, to give people budget recovery time between events.
Being engaged at the same time is fine
Nobody in this thread argued that overlapping engagements were a problem. An engagement is not a wedding. It does not require a spotlight, a season, or a gap. What it does is let you move forward with your life: book venues, find a dress, have the legal conversations that matter to you and your partner.
One person made the practical point that being engaged at her sister's wedding actually helped: there were no awkward "so when are you two getting engaged?" questions from family, and she had a ring to show without taking anything away from the bride.
So if your partner is ready and you are ready, there is no reason to hold the proposal in reserve until after your sister's wedding is over.
The "different seasons" approach
The strategy that came up most often from couples who had done this well: pick different seasons. A spring wedding and a fall wedding in the same year feel distinct. The flowers, colors, and feel of the day are naturally different. The photos do not look interchangeable. And the gap between them is usually five or six months, which is generous enough that guests are not scrambling.
One commenter gave a thoughtful breakdown: if your sister gets engaged this summer and books a spring 2027 wedding, you could get engaged in late 2026 and plan for fall 2027. Her pre-wedding events (shower, bachelorette) happen in the months before her date. Yours happen after her wedding, meaning she gets the full spotlight first, and then you get five months of undivided attention before yours. No overlap in the events that require planning energy from your shared friends. Just two happy occasions in the same year.
"There is enough joy and love to go around. But never really enough time."
Where twins need extra care
People who are not twins kept saying "you're overthinking it" in this thread, and they are not entirely wrong about the logistics. But the people who are twins were quick to explain why this feels different than it does for regular siblings.
When you have spent your life being presented as half of a unit, a wedding is one of the few occasions where you get to be the whole point. You are not "the twins" that day. You are the bride. The worry is not that guests will consciously compare the two weddings. It is that the feeling of having your own singular moment will be diluted if the two events blur together.
The honest answer from the twins who shared their experiences: it did not blur together. A wedding is so specific to the couple, the venue, the choices made, the people in the room, that guests do not leave thinking "well hers was better." They leave thinking about you and your partner and the day you had. That is true even when the timelines are close.
The conversation worth having
You noted that your sister has a habit of dropping hints and then expecting you to read them. You also noted that your mom's death left some gaps in how your family handles these conversations. Both of those are real things to be aware of going in.
The most useful version of this conversation with your sister is not "let's plan our timelines together" and it is not "I wanted to let you know my wedding might affect yours." It is closer to: "I'm so happy for you, and I also want us to both have our own full moment. Can we check in on dates once things start taking shape so we're not accidentally stepping on each other?"
That framing puts you on the same team, which you are. You are not competing for a finite amount of family celebration. You are just being thoughtful about the calendar.
The short answer
Get engaged when you and your partner are ready. Keep your sister in the loop on rough timing, not for her approval but out of courtesy. Once dates become real, aim for at least three months of separation, more if you have many out-of-town guests. Pick different seasons if you can. Let the pre-wedding events for each of you happen in clean windows.
You will each have your day. They will feel different because they are yours and hers, not because of careful scheduling. But the scheduling will make it easier for the people you love to show up fully for both of you, which is the whole point.
When you are ready to start nailing down the timeline, vendor lists, and all the moving pieces, MyWeddingDashboard keeps everything organized so the planning feels manageable, not chaotic.