Somewhere around 11pm on a Tuesday, someone types "questions to ask before getting engaged" into Reddit's search bar. Maybe they're three months from a proposal. Maybe they just got a ring and the panic set in. Either way, they end up in r/relationships or r/AskWomen, scrolling through threads that are half-wisdom and half-projection from strangers who've never met their partner.
And here's the thing — some of it is actually really good. But some of it will send you down the wrong rabbit hole entirely.
This article is about figuring out which is which.
Why People Turn to Reddit for Pre-Engagement Advice
It makes complete sense. When you're facing one of the biggest decisions of your life, you want to hear from real people, not a therapist's pamphlet or a listicle that reads like it was written by a wedding planner. Reddit feels honest. The upvotes feel like consensus. The top comments feel like collective wisdom distilled from thousands of relationships.
And to be fair, communities like r/relationships and r/AskWomen have produced some genuinely thoughtful threads on what couples should discuss before committing. People share hard-won lessons. They flag things they wish they'd asked. They're vulnerable in ways that feel useful.
But Reddit also has structural problems that make it a tricky place to get relationship advice — and understanding those problems is the only way to use it well.
The Most Upvoted Pre-Engagement Questions on Reddit — Analyzed
Financial Questions Reddit Gets Right
If there's one area where Reddit consistently delivers, it's money. Threads asking "what should couples discuss before engagement?" almost always surface some version of these:
- Do you know each other's debt situation?
- Are your spending habits compatible?
- Have you talked about whether to combine finances?
- Do you agree on financial goals — homeownership, retirement, kids' education?
This is solid advice. Research consistently shows that financial incompatibility is one of the leading drivers of relationship conflict and divorce. Reddit users who've been through painful breakups or divorces often cite money as the thing they wish they'd talked about more honestly. So when these questions dominate the top comments, that's the community doing its job.
If you haven't worked through these yet, the questions you should be able to answer before you say yes covers financial alignment in depth — including the specific conversations that tend to get skipped.
The Dealbreaker Questions That Keep Appearing
Another category Reddit handles well: the non-negotiables. Do you both want kids? Where do you want to live long-term? How important is religion in your daily life and in raising children? What's your relationship with each other's families?
These are legitimately important. And Reddit deserves credit for surfacing them loudly, because a lot of couples in the early stages of a relationship avoid them precisely because they're uncomfortable. The questions to ask your boyfriend that matter most are often the ones that feel risky to bring up — and Reddit normalizes asking them.
Where Reddit Advice Falls Short
Survivorship Bias: You're Hearing From One Side
Here's the structural problem with Reddit relationship advice: the people most likely to answer a thread about "what you wish you'd asked before getting engaged" are people who got engaged and then had something go wrong. Not the couples who asked the right questions, communicated well, and are happily married. Those people aren't on Reddit at 11pm writing cautionary tales.
This is survivorship bias, and it warps the advice you receive. The questions that appear most often aren't necessarily the most important ones — they're the ones most associated with visible failures. That's a meaningful difference.
So when a thread is dominated by "make sure you know their relationship with money" or "ask about their exes," it's partly because those are genuinely important topics and partly because those are the topics that blew up spectacularly for the people answering.
Questions That Sound Smart but Miss the Point
Some Reddit-popular questions are technically good but practically useless without follow-up. "Do you want kids?" sounds essential — and it is — but a yes/no answer doesn't tell you how your partner thinks about parenting, discipline, sacrifice, or what they'll do if fertility is a challenge. Reddit threads often reward the question without examining the depth of conversation needed to actually answer it meaningfully.
Similarly, "do you know each other's debt?" is a starting point, not a destination. Knowing the number matters less than understanding the pattern — how did the debt happen, what's the plan to address it, and how does your partner feel about financial risk?
The Emotional Readiness Questions Reddit Rarely Asks
This is the biggest gap. Scroll through even the most upvoted pre-engagement threads and you'll find very few questions about emotional readiness — not emotional compatibility in the abstract, but the specific capacity to grow, repair, and show up consistently over decades.
Questions like:
- How does this person handle being wrong?
- What do they do when they're scared or overwhelmed?
- Have you seen them at their lowest, and do you like who they are there?
- Do they take responsibility, or do they deflect?
These are harder to ask and harder to answer. They don't fit neatly into a Reddit comment. But they're often more predictive of long-term relationship health than whether you've discussed your 401k. For a deeper look at this territory, deep questions before getting engaged covers what emotional readiness actually looks like in practice.
What the Best Reddit Threads Get Right That Most Lists Miss
To be fair, the best threads — usually the ones with hundreds of thoughtful comments rather than a quick top-10 list — do surface something valuable: the importance of process over answers.
The most insightful Reddit users don't just ask "have you discussed X?" They ask "how did that conversation go?" Because the content of what you agree on matters less than whether you can actually talk about hard things together. A couple who disagrees about finances but communicates openly is in better shape than a couple who agrees on paper but has never had a real fight.
This framing — conversation quality over checkbox completion — is genuinely useful and worth taking from Reddit. It aligns with what relationship researchers have found about what actually predicts long-term success: not compatibility on every issue, but the ability to work through disagreement.
And the best threads also remind you that things to discuss before getting engaged aren't a one-time checklist — they're an ongoing orientation toward honesty that either exists in your relationship or it doesn't.
How to Use Crowdsourced Advice Without Letting It Replace Your Own Judgment
Here's a framework I think actually works:
1. Use Reddit to generate questions, not to evaluate answers. Reddit is excellent at surfacing topics you might not have thought to raise. Use threads as a prompt list, not a verdict. Your relationship has context — history, nuance, specific dynamics — that no anonymous thread can account for.
2. Filter through your own relationship's specific gaps. If you already have deep, ongoing conversations about money, skip the financial questions and look for what you haven't talked about. Reddit threads are comprehensive by design; you don't need to cover everything on the list.
3. Notice what makes you uncomfortable — and go there. If you're reading a thread and skipping over certain questions because they feel too hard to bring up, that's information. The avoidance is the point. Those are probably the conversations worth having.
4. Don't mistake upvotes for universality. A question that resonates with thousands of Reddit users might be completely irrelevant to your situation. And a question that barely got any engagement might be exactly what you need. (This is where pre-engagement questions vs. premarital counseling is worth reading — a professional can help you identify what's specific to your relationship, not just what's popular online.)
5. Bring the questions into real conversation — not interrogation. Reddit threads sometimes read like a checklist to run through before signing a contract. That's not how good relationship conversations work. The goal is genuine curiosity and mutual exploration, not a pass/fail audit.
The Questions Worth Taking From Reddit — and the Ones to Leave Behind
Take these:
- How do we handle financial decisions together, and do we agree on our approach to debt and saving?
- What does family look like to each of us — how often do we see them, how much do they influence our decisions?
- How have we handled our biggest conflict so far, and are we both satisfied with how it was resolved?
- What does each of us need when we're stressed, and can we provide that for each other?
- Have we talked about where we want to live, and what happens if one of us gets an opportunity somewhere else?
Leave these (or go deeper than them):
- "Do you want kids?" — too shallow without exploring how and what if not
- "Do you know their exes?" — interesting but rarely predictive of much
- "Have you met their family?" — meeting them is different from understanding the dynamics
- "Do you agree on religion?" — agreement on labels matters less than agreement on how it shapes daily life and parenting
The honest truth is that Reddit is a useful starting point for anyone doing research on pre-engagement conversations. It's full of real people sharing real experiences, and that has value. But it's also shaped by who shows up to answer, what gets upvoted, and what kinds of stories feel satisfying to tell — which isn't the same as what actually matters in a long, healthy relationship.
So take the questions that feel relevant. Bring them to your partner with genuine curiosity. And trust that the conversation you have together will tell you more than any thread ever could.
A good next step: work through the questions you should be able to answer before you say yes — it's built to go deeper than a Reddit thread, and it's organized around the conversations that actually move the needle.