Looking to hear feedback and thoughts about the right time to propose. 26M and 25F. We will be at 2 years of dating in November. We have been living together for almost a year and our relationship has been great- I love her family and she loves mine. We even just got a puppy together. I am beginning to start to think about proposing sometime next year.

For some background, we have a lot in common, similar humor, and have had very few issues and fights. We both have extremely stable careers and no debt. We split expenses. We are both very happy and have been through a lot together in our time dating (she lost her dad unexpectedly last year and both of us had really unlucky and unrelated health scares that turned out to be fine). She dealt with depression for a while after her dads passing and it’s been inspiring to see her heal. Most of our friends are beginning to get engaged and many have been dating for a long time. We have both discussed that we’d like to someday get married and have a family together.

However, it is worth nothing this my first long term relationship and things have been moving fast! She had previously been in a 5 year relationship, and has told me she doesn’t want me to wait forever to propose, but has never threatened or put too much pressure on me. She’s joked that “3 years is her limit!” Her mom has a very expensive and beautiful ring that she has told me I can have to propose with if I decide to marry her (saving a lot of $ there!).

I tend to be a bit conservative with long term decisions and often think worst case scenario. I care a lot about personal finances and planning for the future. I also can’t help but compare relationship timelines to other people- it’s just how my brain works. It seems to me I am moving faster than most of my peers with my relationship, but i am starting to believe I just got lucky and met the one at an early age. I always thought I was bad with women because of my lack of prior long term relationship experience. I always thought I’d be someone to settle down and get married in my 30s. I used to criticize people in there early to mid 20s who moved fast in relationships. But my thinking has changed a lot and I think I’ve matured. I believe I have been slowly changing for the better (less partying, better decision making). And no big sacrifices have been made at the expense of my happiness!

One thing worth noting is that she has mainly been the one pushing for the big decisions. I’ve always been hesitant and anxious but eventually caved and have not regretted them at all.

I would like to propose sometime later next year (always told myself I’d wait at least 3 years, but am softening on this) and get married in 2025. She has hinted at 2024. We both would like a large wedding (my family is unfathomably huge) at a solid venue. Our families are both upper middle class so it shouldn’t be an issue. I know people who wait longer to get married have much lower divorce rates, and this has really stuck with me. Weddings are also expensive as fuck and I want to buy a house in the next 2-4 years.

So my question is, should I hold my ground and wait to propose until later next year or should I do it sooner than later? Is it better to wait just in case things change? Am I overthinking or being impulsive?

I always enjoy feedback and advice. Would love to hear what people think as well as their own experiences. And if anyone has feedback on timelines from engagement to wedding day. It’s a good problem to have!

1 comment
  1. I think you did get lucky, so make the most of it.

    Timing is everything and it sounds like you and she are both ready. Don’t hold yourself to arbitrary time frames and dates. Each person and relationship is different. The statistics on ages and lengths of time are just after-the-fact-averages, they do not mean you will be more successful if you adhere to them.

    If it’s going to happen anyway, you don’t want to sow unnecessary discord by wait for her to become frustrated, or feel like she is pushing you, or that you are reluctant to commit.

    If I were you, I would pick a significant day by the end of this year, like xmas, or new years or her birthday, etc. and propose in some creative, romantic way, with the mom’s ring. It will flatter her mom and her too.

    Once you are engaged, you can schedule the wedding itself at your leisure – 2024 is plenty far enough out. One year earlier won’t make any difference for the marriage, but it will make her feel good to know it is in the plan. Also, she and the mom will get to have their wedding planning fun that much sooner.

    However, don’t do anything you are not comfortable with.

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