Are you ever bored of the same old questions that come up in small-talk conversations over and over again? I am!
I ran across this article of 55 great ice-breakers recently, and it was perfect timing. I’ve been planning to do a “get to know Jess” post because you guys are always asking for more personal content (which, by the way, I can’t even to begin to tell you how flattering that is!) but then I thought–why don’t I answer a few of these awesome “get to know you” ice-breaker questions instead? That’s muccchhh more interesting!
I picked out a few of my favorites, and shared my personal answers to them below. Bookmark a few of these before your next group dinner, party, or even a date. I guarantee your conversations will be much more interesting and meaningful!
Bonus: When you get to the bottom, I’d love for you to pick one of them and answer in the comments below!
10 Ice Breakers to Really Get to Know Someone:
1. What’s one thing your mother/father taught you that completely changed your life?
“You can do hard things” my mother used to tell me over and over again growing up. It’s such a simple phrase, but it really did instill in me the attitude that I am capable of accomplishing anything as long as I work hard enough–no matter how hard it is.
2. What’s been on your mind lately?
Work is on my mind 99% of the time, but right now there’s more of a family/work struggle than usual. There are so many great things happening with the blog and I feel like I’ve finally hit this really great rhythm and momentum in my career, but I always have this feeling of being pulled in so many directions and just trying to keep my head above water. (I’m sure you can relate, right? So many of us go through this!)
Right now, I’m working through that coupled with the guilt of being so far away from my family in Oregon, which has been weighing on me more than usual lately as we’re currently dealing with some hiccups, like all families do at different points.
I’m never going to be able to do things like pick up my nephews or niece from school when my sister could use an extra hand, or pop over to my mom’s or sister’s house for dinner on a Tuesday. I’ve been thinking about this more lately than I have in the past. I have a lot of conflicted emotions about it, because on the flip-side, I don’t really have any desire to ever live in Oregon. Chicago is our home, and all of our friends and Neal’s family are here–but it’s still hard just the same!
3. What’s the first career you dreamed of having as a kid?
The one I distinctly remember most is telling my third grade class that I wanted to be a Sea Animal Trainer at Sea World 😂. I’ve always been a huge animal lover! After that I wanted to be a horse trainer (I grew up riding my whole life). Then after that, a Fashion Designer. I used to have my own sewing machine and I’d make clothes all the time–most notably clothes for my dog–because sure, that’s a normal thing for all 13 year olds to do, right?
4. What’s the last text you sent?
A group text to two of my best friends (the one’s I’m going to Mexico with in a few weeks) that said, “HAHAHAHAHA” 😂
5. What’s one of your favorite memories?
Growing up, my family had a lake house in this sleepy little town in Oregon called Pine Hollow. It’s where so many of my best memories took place. We had a record player and my dad has always been really into old school country music–he would blast Don Williams in the morning to wake us all up. I’d go out into the kitchen and he’d pour me his breakfast special–fruit loops with a side of peanut butter toast, and we’d eat it on the front deck listening to the waves crash from the early morning boaters and water skiers. I miss that house so much.
6. What’s one thing about you that surprises people?
I’m 100% the same person online as I am in person, but I think there is one thing people are surprised to learn. Everyone assumes I’m super sweet all the time because I’m always cheerful and outgoing and I love helping people by nature, but there is definitely a side of me with an attitude 😂 If you mess with one of my friends, you will see my other side come out REAL quick. I’ve got no problem calling out people who need to be put in their place. I’m also not a sugar-coater–I’m always the one my friend’s ask when they want brutally honest advice, haha!
7. Who, or what, was your biggest teacher?
I actually wrote about it in this post, but I think growing up living in so many places was really my biggest teacher–it made me really independent from a very young age and I think that’s probably the experience that I’ve learned the most from in my life.
That, and of course, being raised by the one and only Lynn Keys 😉
8. What was something you’ve done that made you feel extreme happiness?
Our entire honeymoon trip to Cabo! It was such an incredible getaway after our disaster of a wedding. On top of that, wedding planning was a really difficult experience for me in general. One I was so relieved to be over with. I am not a planner by nature. So it really ate away at me at times. Not going to lie, I’m really glad I never have to go through it ever again 😂. I felt like a 5,000 pound weight had been lifted off of my shoulders.
Our last day of our honeymoon we went to the most romantic place I’ve ever been in my life–El Ferallon–which is a stunning cliffside restaurant with this incredible champagne bar and waves crashing so close to you that you can feel the salty ocean spray. I consider myself to be a pretty happy person in general, but that was the first time I ever remember thinking “I don’t know how I could possibly be any happier. This is it. It doesn’t get any better than this.” You can see more from that night at the end of our honeymoon recap video!
9. What did you have to give up to achieve your current level of success?
I made a lot of sacrifices in the beginning to get my blog to the level that its at currently. I was pretty poor and scrappy. So I basically chose my blog over a social life a lot of the time, because I couldn’t afford both! Had to say no any extra expenses that didn’t contribute to the blog in some way. I ate a lot of cheap ramen and frozen Lean Cuisines. So during that period some of my friendships did get a little rocky. Simply because it’s hard to understand why a 24 year old would want to choose working on a blog that nobody reads over going out with her best friends. In the end, everything worked out! No long term damage was done (except maybe to my liver having to process the high levels of sodium and $5 wine during those years 😂). Still it was worth it. Now I have a career I built from the ground up, and I could not be more proud of it.
10. What’s your guilty pleasure?
I definitely have several, but the first one that comes to mind is a big bowl of pasta and a dirty Grey Goose martini (I just recently got into dirty martinis. I LOVE them!) preferably at our favorite neighborhood Italian restaurant, Club Lucky. Others would include pizza and Roseanne re-runs 😂 (I’m so excited Rosanne is back!! I haven’t watched it yet though, have you!? I’ve heard it’s amazing. I think I’m going to watch it tonight!)
Your turn! I’d love for you to pick a favorite question and answer it in the comments, so I can get to know YOU better, too!