(Closed) Thinking about "leading" my SO on….

posted 5 years ago in Honeymoons
Post # 3
12023 posts
Sugar Beekeeper
  • Wedding: May 2014

@cmoest:  as long as he’s not going ot try and surprise you with a prepaid excursion in cancun then i think it’s a fantastic idea!

Post # 4
5 posts
  • Wedding: July 2014

My dad did this with my mom and she loved it.  They were going to stay local for their honeymoon as they were a new couple and couldn’t afford anything else…but he saved up separately and surprised her with a cruise to the caribbean the week of their wedding (so she could pack).  


But as the other poster said….make sure he’s not super excited about a beach vacation, if you’re planning a trip to the windy city.

Post # 5
12248 posts
Sugar Beekeeper
  • Wedding: May 2013

That’s really sweet! How long is your honeymoon going to be?

If it’s like a week, Chicago would be fun! But if it’s longer, I might stick to Cancun!

Post # 6
567 posts
Busy bee
  • Wedding: October 2013

Sounds like he’d love it, but make sure he deals well with surprises or unexpected changes. I’m actually terrible when I expect one thing and get another. For example, when Fiance proposed, he took me to a concert in the park. I didn’t know he was going to propose (I had a feeling, but wasn’t sure) so mostly I was just excited about the concert. He proposed right before the concert and I was SO THRILLED and unbelievably excited and happy and appreciative of how he did it, but I have to admit I was a little disappointed when we left the concert early to go celebrate. I had it in my head that we were seeing a concert, so having something different than what I expected threw me off. Of course, I didn’t tell Fiance this, and it was still an amazing, as close to perfect day as you can get, but it still nagged at me a little. It wasn’t about the concert, per se, but the expectation for the day that wasn’t met. I’m terrible at surprises because I like to plan.

Post # 7
11272 posts
Sugar Beekeeper
  • Wedding: April 2012

@cmoest:  depending on how long your honeymoon is and when the games are on, i’d surprise him with both.  fly to chicago for the game, stay a couple of days and then fly out of chicago to cancun for a week.


@MsGinkgo:  that’s the first thing i thought of too.

Post # 8
3731 posts
Sugar bee
  • Wedding: September 2014

@cmoest:  A whole week in Chicago might be too long in my opinion. I think a long weekend (Friday through Monday) would be a better amount of time. I like the idea of surprising him! Who wouldn’t LOVE that?!

Post # 9
2489 posts
Buzzing bee
  • Wedding: June 2017

Chicago is a great place- I’ve been there at least a dozen times, if not more.  There is a ton to do, especially in the summer/early fall, because then you can hit up the outdoor attractions.

But it is VERY different from Cancun.  So make sure it’s not, like, the day before your trip that you’re going to surprise him.  Otherwise, he’ll be packed for the hot beach instead of the mildly cool early fall midwest.

Post # 10
10367 posts
Sugar Beekeeper
  • Wedding: September 2010

Why don’t you go to Cancun still, and also give him Cubs tickets for a different trip? Is that possible? I just feel like Chicago is such an easy trip to do at a different time.

Post # 12
8690 posts
Bumble Beekeeper
  • Wedding: October 2013

the cubs and chicago could be done anytime.  make sure the cubs are intown when you want to go.


Post # 13
8042 posts
Bumble Beekeeper
  • Wedding: December 2013

Well… in some ways I think it’s an awesome idea, but what if now he is looking forward to Mexico?

I guess when I have something in my head and I start to look forward to it, most things would disappoint me (yeah, even if it was something I really wanted to do). I hate when plans change… especially if I didn’t change them myself. I don’t like surprises either.

You know him best. I think it’s a sweet gesture… but at the same time, you’ve always wanted to go to Cancun, and it might be nice to just relax on the beach vs. see the sights in Chicago.

I would really think through the logistics. I know in my relationship it would be impossible to hide something like this lol. Shared finances and all! It’s hard enough hiding a Christmas present ๐Ÿ˜‰

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