(Closed) Curious conversation starters

posted 5 years ago in Waiting
Post # 3
1502 posts
Bumble bee
  • Wedding: May 2014

He first brought it up (after a couple years of hypothetical wedding/future talking) last summer, and asked “Can I ask you something?  Do you want to get married?”


Since then, a lot of friends have become engaged and we’ve attended several weddings.  The wedding talk usually stems from that.

Post # 4
2390 posts
Buzzing bee
  • Wedding: July 2011

I wish I could remember!!! He proposed after we’d dated for 2 months, but it wasn’t a surprise – we knew before that that we were getting married. It’s weird that I don’t remember talking about it though.

Post # 5
40 posts

Very early into dating, he randomly said, “Do you think we could end up married? I can see that happening.” lol. After we both settled into jobs, it slowly came up more and more until we were actively talking about. 

Post # 6
5885 posts
Bee Keeper
  • Wedding: October 2010

From the beginning we talked about hypotetical, “I want this or that when I get married” (we were late 30’s). Not specifically about the other person, but we needed to know if we were on the same page. 

After dating 10 months, I basically told him when my lease was up when we had been dating 1.5 years, we would either be engaged and planning our wedding or broken up and I was buying a condo. At that point I would be almost 40, at 1.5 years, you either know or not. I wasnt going to waste my time. He was kinda shocked and we didnt talk seriously about it for another 2-3 months. He knew it wasn’t an ultimatum, it just was a fact and I was totally okay if he didn’t want to be married. Better to know sooner rather than later.

I think women dance around the topic too much. If a guys loves you and is mature (late 20’s+), he should be ready to at least have the “are we on the same page” conversation. If that scares him off, good riddance!

Post # 7
625 posts
Busy bee
  • Wedding: August 2012

I suppose it was sort of a gradual thing. He started joking around about it two months in… nothing too serious. But I did tell him that there was a deadline to my relationships… That I was not willing to wait forever to get engaged, nor was I willing to have a forever engagement. I told him that I would wait three years max… and if we didn’t know what we were doing at that point, then there would be no point in continuing. This was mostly said in comparison to other people we would hear about, but he got the message. I also told him that I refused to start planning before I knew it was for sure, so eventually (around the two year mark?) we started having conversations about whether or not he wanted this to happen. I started eyeing wedding magazines in the stores, and watching SYTTD… and eyeing him as well, slowly applying pressure for an answer one way or the other. Eventually, I said “Hey, listen, I’d like to have an August wedding. Weddings take about a year to plan. It’s July now. So if you want to get married, you need to give me the go ahead soon, otherwise we’ll have to put it off another year. So he told me to start planning, and we bought the ring when we had the money.

For me, it’s all about communication and intention. Marriage is something I take seriously, and finding a life long partner was a big priority in my life. I made that intention clear in the beginning… but let things grow on their own past that (I wouldn’t bring it up at all for huge chunks of time). It wasn’t until we were getting closer to our “deadline”, and had been living together for about a year, that I really started to want clarification on it.  

Post # 8
1669 posts
Bumble bee
  • Wedding: August 2014

We started talking about marriage in broad terms at first after about 6 months of dating (he brought it up) and then sort of loosely started talking about “when we get married”.  When we started talking about living together, we decided that engagement had to be imminent before we took that step. Then a few months ago (right before he moved in) we sat down with some wine and marked out a timeline of things we wanted (kids, marriage, etc) and discussed expectations for engagement. He asked if I’d be comfortable helping him pick out the ring, and told me the two months that he’d propose in. I think he’s going to attempt to surprise me though since we are both hyper type-A planners surprises are not our thing.

Post # 9
1112 posts
Bumble bee

He brought up getting married a few short weeks after we started dating. Haha. We had been best friends for over 3 years, and we both unspokenly knew we’d get married on the night he asked me out. So it wasn’t strange. So for the 3+ years we’ve been together, marriage/the future has always been a conversation topic. I think that was healthy for us. 🙂

Post # 10
1069 posts
Bumble bee

We have talked about getting married ever since we first started dating, and every time he has always brought it up. He would joke in the beginning of the relationship about how he wishes we could just run off and elope and he would always comment on what my new name would be (it’s cute sounding). 

Post # 11
2130 posts
Buzzing bee
  • Wedding: July 2016

My SO bought it up about 4 months into our relationship. If he hadn’t bought it up, I think I would have bought it up after our 1 year anniversary. And I would have just simply asked him where does he see our relationship heading…

Post # 12
1606 posts
Bumble bee
  • Wedding: August 2013

@Kat_Kit2000:  I used this. I think the main reason he took so long was because he couldn’t get his head around it. I asked questions when things were going good and the mood was calm and positive. I think it really helped him to get cozy with the idea of ‘forever’ as well as how we would operate as a single unit.

I would ask silly questions on car trips like – who would you ask to be your groomsmen? what do you think about khaki suits? where would your dream honeymoon be? do you like super traditional weddings (white silk and candles) or contemporary, casual weddings (outside, BBQ)?

Just silly non-consequential stuff. The groomsmen thing really got him excited…not sure why but we got to have a long conversation each of his friends and why he thinks the 5 he picked were so important to his life.

I also asked things about how many kids does he see us having (without asking for a timeline) – and then we got onto a fun conversation about baby names. I asked him how long he wanted to stay in his current house, would be buy a new car after kids, how would our bills be handled…account wise and percentage wise.

Lastly, I asked questions on some bigger ticket items…he isn’t currently religious but I asked him if he saw it in his future. I asked him what he would do if his mother were to intrude into our lives, I asked him what his goal in life is if he could define it in single way. I also asked him what his biggest fears were when it came to getting married. (Shockers were that he was terrified of getting a divorce and financial issues hurting us).

Post # 13
446 posts
Helper bee
  • Wedding: March 2014

For us, like many of the people that commented, it was gradual.  A good way to get him thinking about it is to talk to his mom or for her to bring it up to him on her own.  We had been together just over a year when my SO’s mom tried to give him her engagement ring for me.  I think that got him thinking ok, this is the one.

We would go to our friend’s weddings and in the beginning he was mostly there for the party.  But you could tell as we went to weddings after we’d been together more than 2 years that his attitude kind of changed.  He would comment on things he liked, things he didn’t like, bring up “well when we get married, I’d do this differently…”  Conversations stemmed easily from that.

Then after 3 years, I got a lot more serious about wanting to get engaged.  Women look at the future and their timeline and where they want to be a lot more than men do, so you almost have to spell it out for him.  I told him I want to be engaged at least a year and 27 years old when I’m married.  That way there’s a couple years to enjoy eachother before I start feeling the pressure to have kids.

So I told him “by June.”  That was last December.  In February we started shopping for engagement rings and now I know that he’s working on getting one.

Don’t feel awkward about bringing it up.  Like another poster said, I would watch SYTTD and comment on what I liked and didn’t like and that would start the conversation.  There are little things you can do.

Also, a little liquid courage never hurts.  Have a night at home with dinner and a bottle of wine and just kind of ease into it.  Maybe start with talking about how happy you are in the relationship.


Post # 14
1540 posts
Bumble bee
  • Wedding: July 2015

We started dating at 20 years old and neither of us wanted to get married that young, but we were serious very early on. We started saying things like “I wanna be with you forever”….stuff like that. Slowly things about marriage were brought up but in hypothetical terms. He was very receptive and we would talk about different locations, amount of people there etc…..I never worried that I would scare him away. I knew this was a sure thing, just didn’t know when.

Last year when we got to our 5 year anniversary, I felt more ready to get specific. I told him that 5 years is a long time and I wanted more than just “some day.” We discussed both of our concerns and he realised how important marriage was to me. See, he always knew we’d get married, but (because he’s a man) he probably would have been happy to wait until our 10 year anniversary to get engaged lol. I obviously had to express my feelings

As a pp said, having some liquid courage is a good thing. My SO was fine talking about marriage stuff as long as I didn’t try chewing out a timeline. I’d say if you wanna talk about wedding stuff than do it! Just go by his response. If he’s obviously turned off by the idea then don’t talk about it as much

Post # 15
4523 posts
Honey bee
  • Wedding: September 2014

@Kat_Kit2000:  After dating for 7 months, SO asked me to move across the country with him.  I asked him why and he said “I never thought i’d get married, I thought it wasnt going to happen for me. Then i met you and I know I have my best friend”


……and I really bet he regrets ever saying that, because I’ve taken it as an invitation to bring it up for the last 2 years 🙂

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