Millennials, 5 Conversations To Have Before Getting Engaged

Millennials, 5 Conversations To Have Before Getting Engaged, simple engagement rings, relationship tips and advice, struggles and truths for dealing with issues with boyfriends or girlfriends, how to know if you're ready to get engaged, #relationshipgoals, #relationshiptips, #engaged, #engagement, #engagementrings, #relationshipadvice
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While I am by no means a relationship expert, I had my fair share of relationships before tying the knot with the hubs. Lately, I've been noticing a trend amongst my friends where pressure from the “Facebook effect” has been increasing the “hurry up and get engaged” feels.


Consequently, over the last few months, I have been around one too many engagements falling apart, from one of my closest friends to my next door neighbor. Too often I find myself in conversations with already engaged or soon-to-be engaged people who are completely fixated on their wedding day, even if they don't have the ring on their finger yet. There seems to be this growing trend, thanks to the plethora of reality TV shows, of people obsessing about “the big day.” Many people appear to be forgetting what it really takes to get down the aisle.


While I by no means know 100% what made E and I stick together these last five years, I do know that we talk… like a lot. Like two girls hashing out last night's Bachelor episode a lot.


5 Conversations To Have Before Getting Engaged:

The confused millennial communication-3

E's Glasses*  |  Shirt  |  Joggers*  |  My Grey Long Sleeve Shirt: Similar V-Neck*  | Similar Cold Shoulder V-Neck*  |  Similar Grey Long Sleeve with Elbow Patches*  |  My pants: Fit Physique Lululemon.



Let's start with the obvious: if one of you desperately wants kids and the other could never envision their life with children, then it's time to move on. If you both are on the same page with wanting kids, then now is the time to start talking about parenting styles that you learned or witnessed in childhood. What you liked, what you disliked, and so much more. The decision to have kids is just the tip of the iceberg.

[RELATED] Why I’m Scared To Have Kids [+ How I’m Working Through It]


Religion and values

Even if you aren't super religious, it's still important to have this conversation. E and I were both raised Jewish, but don't go to Temple or anything today. We still talk about what role we want it to plan in our children's lives as well as our views on spirituality and a Higher Power. If you do have a different religion or values from your significant other then consider if you can respectfully agree to disagree. The last thing you want to do is push forward while the resentments and passive aggressive comments only continue to grow internally or from family and friends.

Work-life balance

If your partner and you are not on the same page about your envisioned work-life balance it could lead to some serious fights down the road. For instance, as a blogger I work weird hours sometimes, it'll be 9 pm and I am just busting out my laptop to take care of something I forgot… and work-free Saturdays and Sundays? FUHGETTABOUTIT. Luckily, the hubs had his own company and is a consultant today, so he is working those weird hours alongside me.

[RELATED] 8 Ted Talks On Work-Life Balance You Need To Watch

The last thing you want is to envision yourself as a stay at home mom, while your partner is envisioning the same thing! Or worse, you are staying home and your partner is in the office for 14 hours and you start to get lonely or resentful. The key with this conversation isn't to have it all figured out, but to try to understand one another's visions for the future in terms of career and home life. It's a lot easier to get behind 14 hour work days if you understand the ultimate goal is for your S.O. to be CEO.


Like the work-life balance conversation, the goal here is to get to a place of understanding, not necessarily to have it all mapped out. Ask tough questions about your partner's current financial situation (Are they in debt? if so, how much? Are they saving for retirement? Are they taking care of any other people financially right now? What is their spending style? Do they have a history with overspending or gambling? Does anyone in their family have a history of gambling or overspending?). This will help with not only getting engaged and the wedding planning process but also a clearer picture of whether or not you two are a good match for the future. True story: if your significant other is buy $500 shoes and shipping them to the office so you don't find out, it's probably not a good sign.

[RELATED] How To Talk About Finances With Your Significant Other

The confused millennial communication


Living style

Maybe this one comes from watching a few too many hours of whatever HGTV show is on, but if one person loves modern and the other loves rustic, buying a home or decorating one can get pretty frustrating. While this is probably the least important conversation to have, and certainly not a deal breaker by any means, it's more about how you guys compromise and work together as a team. If you steamroll your partner on every style decision, what else are you going to steamroll them on?



Wedding Day Vision

Sure, the stereotype is that girls have been dreaming about their big day forever, but that doesn't mean you partner doesn't have some dreams of their own. Make sure to have a conversation about expectations or hopes for the wedding day. This could be surface level stuff like the decor, but it could also be more about their vision of who walks who down the aisle, the role family plays in the planning process, and so much more. We decided very early on that we were okay with eloping and paying for a small elopement ourselves, which gave us a lot more freedom to set boundaries when we did decide to have a wedding that was funded by family. In other words, we preferred to elope than accept stuff with a lot of strings attached to it because it would take away from our vision as a couple and also add unnecessary stress to celebrating our love. Which ultimately led to a lot of boundaries with family. All decisions were made as a team, and nothing was agreed to without talking to the other first.

I have had friends hysterically upset because they felt like their fiancé kept siding with family rather than them. Remember, this is about the two of your joining together as one, so start to act like it.

rachel ritlop eric dresdale wedding
Photo Cred:


The Ring

Ok, this is a fun one! Make sure you guys go ring shopping together! Get clear on the budget that you both feel comfortable with too. Growing up my mom and dad fought all of the time because he spent way too much money on her engagement ring. Remember, if your fiancé finances a really expensive ring, that is your money (or debt) too now! I went with E to several jewelers to discuss pricing, cut, clarity, all that fun stuff to make sure it was something we were both happy with. The engagement was still a surprise several months later and it did not take away from the magic of our engagement story by any means.

Brooke Images
Photo cred:


What conversations did you have before getting engaged? Or what conversations do you plan on having before getting engaged? Drop me a comment!

Originally published on 01/18/17


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102 thoughts on “Millennials, 5 Conversations To Have Before Getting Engaged”

  1. All these are very healthy (and long) conversations that every single couple have at a certain point. At least if the relationship is serious. The only topic that does not make me comfortable is kids. Maybe I’m not mature enough yet.

    Cristina | *janded

    1. I simply feel the pressure the society puts upon my shoulders of having kids because ‘that’s what everyone does’ and I don’t agree with it.

  2. Yes to all of these! I’ve been with my husband for about 15 years (married for 1) and we still talk about these things and discover new pieces about each other. It is so important to really have a grasp on the person you are marrying and the similarities/differences you see in the future.

    Clothes & Quotes

    1. Agreed! I love that point, these conversations aren’t one and done, they grow and change as you both grow and change! If you can’t talk about it before getting engaged, then when will you?

  3. OMG YAAAAAAAAAAAAS x a million to this one, Rach! Per usual, you hit the nail on the head and the ball outta the park. Kids = important. Money = important. Religion = important. Even if you don’t consider YOURSELF to be particularly strong-viewed on something, you *need* to know your partner’s feelings, and you have to truly consider all repercussions before moving forward with big decisions like marriage. HECK YES. Sharing this everywhere!

    Coming Up Roses

  4. YES!! My husband and I have been together forever… 17 years…(since high school). Before we got engaged we still asked all of these questions. It’s so important to not only talk about the current future but what you both want and how you see yourself as a couple and family. You really are in everything together-for better or for worse. Mind as well spill the baggage now cause they are going to see it later anyways!

    1. Awe that’s amazing! Definitely agree with the baggage piece! It makes it so much easier to work as a unit when faced with challenges when you understand the other.

  5. This is SO true! Dave and I have certainly talked about all of these. Like you, we were raised in the same religion but neither practice, but we absolutely talked about the role of religion on our future. Dave and I have been together for almost our entire adult lives (I was 20 when we met) so just about all of these things came up naturally at some point.

    1. Awe that’s so sweet and thank you! It’s so important! I am always so surprised by couples who don’t have these conversations before hand, because you are going to keep having them as you both grow and change.

  6. Love this post! These are all great questions to ask since you do want to be on the same page with your partner. Money I think is the biggest one because it can make or break the relationship.

  7. This is a great post! And so important to be reminded to have these conversations with your partner. The way I see it, if you can’t have these conversations now, then when? Especially about money. Yikes! That is the number 1 reason for marital problems!

  8. I feel really lucky I met by boyfriend so young that we have really grown up together, and we know the answer to all these questions! I think these are all so important to answer!

  9. These topics are definitely so important to have with your fiancé! Thanks for sharing, Rachel!


  10. The work-life balance totally hit home with me! My boyfriend works crazy hours…530 pm – 330 am 6-7 days a week while I stay at home with our 1 year old. I tried to get a job outside of his home but because of his crazy hours, and needing to sleep a lot, it just didn’t work out. There was a lot of fighting, loneliness, and resentment at the beginning but honestly the trouble of work outside of the home was way more stressful. So I took it upon myself to start blogging and started my own home business in health and wellness. A good self help book on co dependency also helps a lot! He’s providing for us and actually enjoys working a lot…who wouldn’t with the nice money that comes in. And I am slowly getting use to having me time and learning to live happily with myself. Most people couldn’t do it but it works for us and that’s all that matters. Find your balance is key!

    1. Finding your own balance is totally key! As long as you guys are on the same page and support and understand one another that’s all that matters! What books on co-dependency would you recommend?

    2. Codependent No More: How to Stop Controlling Others and Start Caring for Yourself by Melody Beattie is my favorite plus you can buy a workbook to go with it. She also writes other amazing self help books on other mental and spiritual topics.

    3. Yup I am very familiar with her work. My previous career before blogging was actually as a mental health counselor. I used her books often for client’s treatment work.

    4. She really is wonderful and I love how her books are not filled with fluff but actually have useful and thoughtful text. Self help books are such a wonderful tool.

  11. These are all definitely important topics to discuss before tying the knot! A lot of people fail to bring these things up because they know they’ll disagree and they just want to shove it under the rug, but these incompatibilities can sometimes cause bigger issues in the long run. Great post and advice!

  12. One of our most important conversations was location. My husband is from upstate NY and likes to move around while it was important to me to stay close to family. If your spouse wants to move around and not settle down it can create problems. Great advice!

    Greta |

  13. Aww your’re such a cute couple! I wish I had read this several years ago! Then again I was young, I got married at 22. And I’ll be officially divorced in three weeks! Lol, we live we learn!

  14. Ahh, I love this post Rachel! I liked how you mentioned talking about a work-life balance. Even in dating, it is never ideal when you have different levels of passion/work-ethic than your partner. I also think work styles can mutually compliment and inspire each other. 🙂

  15. Such a great post! Funny, my husband was raised Jewish too but my parents were Catholic/Mormon. The work-life balance one is huge. My hubby is a workohaulic but so am I (with my biz at least) so it balances out haha.

  16. First of all, you two are adorable in all of the pics. 🙂 I agree with all of your points and the big ones are obviously most important (kids, religion, and money). The church I was married in (Lutheran-based) insisted that engaged couples attend a weekend-long camp to discuss all of those issues before the priest would agree to officiate at the ceremony.
    erin |

  17. This is so real. My husband and I are pretty good about talking a lot but we are having a new fireplace put in and I realized I never asked him if he liked my design plans! So I quickly asked his opinion only to find out that I’d never even SHOWED him the designs. He said he trusted my design skills but that was a slap in the face for me that even the best communication skills need work.

  18. These conversations are so important! I think work-life balance and money are two big ones many people forget to have when they’re excited about wedding planning. It’s so important to go over what life looks like after the big day. Also, you two are the cutest!

  19. This is really great advice. Thing like money and kids are super important, but figuring out if you both can compromise is very telling of how married life will be, too!

  20. girl the amount of people my age I see on Facebook getting engaged is stressing me tf out haha. these are all such important things to talk about before any kind of longterm relationship! ps everytime you post a pic from your wedding i die, they’re so so gorgeous ?

  21. This post was very well-timed for me in a way, because a good friend of mine told me just this afternoon that he intends to propose to his girlfriend soon — and they’ve only been dating for three months (and only known each other for four)… yikes, haha. I totally agree with you, these kind of conversations are super important to have before getting engaged and tying the knot!

    Stephanie |

    1. Oh wow! I hope everything works out with them! Is he still planning on proposing? How did they meet? I am so intrigued by couples who move fast!

  22. My fiance and I had all of these plans and tips (: I picked out my ring ironically and we have known eachother for 7 years so as bestfriends we always discuss everything! Great post because it is super important to have this type of communication.

  23. Yes! Agree with all these! Any slight disagreements can get bigger and bigger if you don’t address them early on and that’s no fun! Great advice for couples just starting out. 🙂

  24. These are all so important to discuss!! I think you’re right about the social media pressure. People need to really get to know each other and talk through these things before making such a big commitment!

    1. Yup! It’s so easy to get “Wedding fever” or “baby fever” or “puppy fever” from social media! Its a slippery slope!

  25. Yes, yes and yes. Me and my boyfriend (hopefully soon to be fiance) are on the same page with all these things. We are very open in communication and talk about our future everyday! I feel if a couple can’t have that, then you need to challenge yourself to have those conversations.

    Meghan |

  26. You shared such helpful tips, Rach – I feel like so many people become obsessed with the idea of marriage itself without really looking into everything that’s involved with it. Love this!

  27. I’ve noticed the rise in wedding-talk, too, and I agree that a lot of people seem more fixated on the wedding day than the marriage. Conversations like these, and in-depth conversations in general, can make a big difference in ensuring that you’re really ready!

    Sara | Sara Laughed

  28. I love all of these! My BF and I have been together for almost 5 years and we are in NO rush to get engaged or married! We always tell people we have better things to be doing (right now) instead of getting engaged But that totally doesnt mean we haven’t talked about all of these! We both have similar views on all the things you mentioned, and I think every single one of them is a huge thing to discuss before getting engaged or moving in with someone!

  29. I love this post! I am not engaged or will be any time soon but soooo many of my friends are getting engaged. It’s super important to have these types of conversations. My boyfriend and I have talked about a lot of these things and have the same vision for our future but many of my friends have not and it scares me for their future. I definitely want to share this post with them!

    xoxo, Hannah

    1. Thanks Hannah! I definitely surprised me by how many of my friends weren’t having these convos. It can be easy to get caught up in the hustle and bustle of life, but there should always be time to talk about the future!

  30. Yes yes YES!

    We’re not planning the wedding yet (well sort of) but we’ve already had all of these discussions. Kids was the first thing we discussed at just about 1 year… we didn’t even talk marriage for another year and a half but it felt good to know we were on the same page.

    We check in with each other regularly on this stuff too. We’re big talkers in our house!

    Great advice Rachel 🙂

    Laura @

    1. Thanks Laura! It’s so nice when you have someone who talks a bunch with you, isn’t it! haha

  31. We had all of these same conversations before we got engaged. Another conversation we had is about our kids’ education and where we stand with that.

    1. That’s a good one too! I lump that into parenting style and it’s hard to know exactly what is going to happen with education systems in the next several years (at least in our county)

  32. Kaitlyn Fickle Killebrew

    These are great talking points before someone plans to tie the knot! Nick and I definitely discussed all of these

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