Honestly, getting engaged last year felt amazing, but the big “Are we ready?” question started lurking. Saw tons of vague advice online, felt useless. Decided me and Natalie needed actual, concrete talk, not fluffy stuff. Wanted real questions to dig into reality.
First, grabbed a giant pad of sticky notes, the kind you see in office meetings. Sat down at our tiny kitchen table one rainy Saturday morning, coffee steaming. Told Nat, “Alright, no distractions. Let’s figure out what we need to hash out before saying ‘I do’.” Felt a bit like planning a project, honestly.
Building the Question List (The Messy Start)
Started totally blind. Just yelled out stuff that popped into my head:
- “How do we handle arguments now?” (We both scribbled this instantly)
- “Seriously, money. Who pays for what?”
- “Kids? Like, how many? And when?”
- “Where are we gonna live long-term? Your city? Mine?”
- “What are our deal-breakers?” (That felt heavy)
- “How much time do we need apart? Hobbies? Friends?”
My sticky notes looked like a rainbow explosion gone wrong. Nat started adding her own, super practical ones:
- “Who does the dishes? The laundry?”
- “What about holidays? Rotate families?”
- “Health stuff? Future care ideas?”
- “Career goals – will moving screw things up?”
Took us a good hour just to brain dump. Had to peel off notes, rearrange them, group similar stuff. Ended up with messy clusters like “$$$”, “Family/Kids”, “The Daily Grind”, “Big Dreams & Fears”. Looked chaotic, but it was our chaos.
Actually Asking the Questions (Awkward & Real)
This part wasn’t Instagram-perfect. We picked a cluster each weekend. Started easy-ish with “The Daily Grind”.
“Laundry,” I asked, trying to sound casual. Nat laughed, “Okay, fine. I hate folding. You fold?” Deal. But then came harder ones.
“Deal-breakers.” Took a deep breath. Mine was “No secrets about finances. Big debt? Gotta be upfront.” Nat went quiet. Turned out she had student loans she hadn’t shared fully. Not deal-breaking, but oh man, the tension. We talked salaries, debt numbers, future savings plans. Coffee went cold three times during that talk. Wasn’t pretty, but necessary.
“Kids?” was another biggie. Thought we were aligned. Found out Nat was more flexible on timing, while I had this “before 35” clock ticking. Took weeks of smaller talks and “what ifs” to really understand each other’s stress points, not just the headline answer.
The Ugly, Uncomfortable Bits
Didn’t breeze through. One weekend tackling “Career Goals & Sacrifices”. Nat mentioned a dream job overseas. My gut reaction? Panic. “You never said!” She thought I knew she wanted international work. Felt like we were talking different languages. Felt stuck. Had to step back, ditch the sticky notes, just vent. No solutions that day, just hearing each other’s fears. Went to bed kinda grumpy. Needed space to process.
Key learning? Not every conversation wraps neat. Some answers are “We don’t know… and need a plan to handle not knowing.”
Where We Landed (No Perfect Score)
After weeks, the sticky notes migrated off the table onto a big poster board. Organized them into:
- Stuff we AGREED on (Laundry! Holiday rotation!)
- Stuff we COMPROMISED on (Kids timeline midpoint, budget adjustments)
- Work-in-Progress (WIP) (The international job possibility – needing more career clarity first)
- Non-negotiables Clear (Absolute honesty about $, no abuse ever)
Wasn’t about hitting 100% agreement on everything. More like uncovering the map of our relationship. Knowing where the safe paths were, the rocky areas needing bridges (the WIPs), and the cliffs to avoid (the non-negotiables). Felt calmer, way more grounded. The wedding felt less like a leap and more like a next step we’d actively prepared for.
Biggest takeaway? Talking is work. Raw, honest conversations are tough. But seeing it mapped out? Priceless. Knowing we could navigate the tough stuff together – that was the real “ready” feeling.
