UPDATE: This giveaway is closed. Thank you for your interest in Using Our Words and UrbanSitter!
I’ll be honest. When I hear the term “date night” I kind of roll my eyes. But recently, when talking to a friend, I was forced to admit that my snarky response isn’t because I wouldn’t love a fun night out with Lenny now and then. I mean, I happen to think he’s fabulous…and escaping our house isn’t all that bad either. No, it’s because there are times the effort just doesn’t seem worth it. There’s the getting all cleaned up. There’s the finding the babysitter. There’s the telling the kids (who think time with you is better than just about anything in the world even though watching you do laundry isn’t really all that exciting) that you’re leaving them. And then there’s the paying the babysitter.
Well, I got the chance to chat with Lynn Perkins, CEO of UrbanSitter, and she put all my excuses to shame (in the nicest way possible, of course). And, she wants you to get out of the house too. Which is why I’m working with UrbanSitter to give away 5 $50 gift cards toward babysitting (details at the end of the post). I have a feeling after you read what she has to say, you’ll be running to check your calendar.

Date night. It sounds great, but we’re busy. And tired. And like our couch and DVR too much. What’s a realistic goal for how often to plan a date night?
Start off slowly. Aim for a date night every other month, then more frequently after that. It’s okay to be realistic; not every couple needs or wants a weekly date night commitment.
Date night doesn’t have to be at night when you’re both tired, why not try a Sunday brunch date? Need more motivation? Plan a double date with friends for added accountability—and if your friends have kids, you can share a sitter.
Our kids are super (like super, super duper) sensitive and get nervous about new people coming into our house. How do you suggest preparing them for a new sitter?
Get the kids involved in choosing a sitter. Discuss what sort of qualities a great babysitter has. The kids might say they want a nice babysitter, a pretty one, or one who likes coloring. Even if none of the suggestions are realistic, your kids will feel heard and you might gain new insight.
Ease into it with a “working interview,” where you’re home doing chores while the sitter and kids get to know each other. This is a great way to introduce someone new and build familiarity.
How can we prepare the sitter for our kids’ temperament and (strong, strong, strong) possibility of tears when we leave?
Separation anxiety is very common and most sitters have their own tricks of the trade to dry teary eyes. While there is no such thing as a foolproof plan, parents can try a few tactics:
Put the kids in charge! For a kid, what could be better than being THE expert in your home on where things are and how things work? When the new sitter arrives, put your child in charge of “helping” and teaching her everything she needs to know. Where are the crayons? When is bedtime? How does Fido like to be pet? If your kids are busy being in charge of making the new sitter feel at home, they may not notice their own apprehension.
For young children, make sure your child’s favorite toy or lovie is on-hand when you make your exit. Let your sitter know which distractions work best to calm your child down. Does heading to the backyard for fresh air and the sandbox usually do the trick? Arm your sitter as best as possible, then give the kids a big hug and make a swift exit.
Have an itinerary. Consider putting together a list of the day’s activities: lunch, coloring and crafts, walk to the park, stop for ice cream. If you think your kiddo will like having a predictable plan to follow, ask the sitter to keep the activities in sequential order. That way, she and the child can talk about and look forward to what comes next.
Bend the rules. Many parents like giving babysitters some leeway when it comes to “breaking” the house rules. This automatically sets the sitter up to be the fun one who lets the kids get away with things that Mom or Dad normally don’t, and creates within the child an association between having a babysitter and getting some special perks! Think about some of the normal rules you’re willing to bend a little: A later bedtime? Dessert before dinner? Chances are, the sitter will love you for it too.
Inevitably, when we do get out, our date conversations turn into talk about the kids. Do you have any ideas for activities or conversation topics that would change things up?
Play the “What if…” game together. What if we retired tomorrow, where would we live? What if an extra $100,000 landed in our laps? Run a few fun scenarios by each other, you might be surprised to hear one another’s replies!
Start your date night with something more than just dinner—go to a local lecture, see a local band, pick a restaurant with a type of cuisine you’ve never tried, pick a wine bar with tasting flights, watch a movie—that way, you’ll have lots to chat about over dinner.
Brain feeling fried? Nothing’s more entertaining than seeing your significant other put on a pair of bowling shoes—and it’s okay to simply enjoy each other’s company and have fun!
Great stuff, right? And what’s even better is a chance to have the babysitting for your night (or day!) out covered. Here’s how…
GIVEAWAY DETAILS: This giveaway is open to new users of UrbanSitter in the US. There are two ways to enter for a chance to win one of five $50 UrbanSitter gift cards. You may enter once for each option for a total of two entries per person. Entries close Wednesday, March 18, 2015 at 11:59pm PDT. Five winners will be chosen at random and notified by email.
1) Leave a comment on this post. What would you do if you got a date with your mate? When was the last time you went out sans kids? What’s your favorite thing to do for a date night? How do you make the sitter the hero?
2) Subscribe to get Using Our Words posts sent to your inbox. Enter your email address in the subscribe box at the top right of the site and confirm your subscription when you receive the confirmation email. If you don’t confirm, I won’t get your entry!
Disclosure: I received compensation from UrbanSitter to write this post. All opinions are my own.
Great suggestions! We’ve finally gotten in the habit of semi-regular date nights. It really is a great way to fall in love with your partner all over again. We’re lucky to have lots of family nearby so the sitting thing isn’t usually the barrier for us.
Sounds awesome!
Date night sounds amazing – I’m in!
I love Urban Sitter. We just hired a fabulous nanny for the boys. I plan on using her on the weekends too if needed.
Our favorite thing to do is go to the Rosewood on a Friday night. Have dinner by the pool and just relax.
Our last date night was a few weeks ago and it was only a semi- date. We had one out of three kids with us. It felt relaxing either way!
Would take a bottle of champagne + a couple of glasses, climb up Mt Davidson and watch the sun set on the city.
Urbansitter sounds great. And date night too! Great interview Amy!!
Free babysitting? Sign me up!
Date night! Woo-hoo! We have managed 4 nights out in the 20 months we have lived here! We would love to go to dinner and a movie! Or just a movie! Or a cup of coffee! Or pretty much anywhere as long as we were together! 🙂
We need a brunch date!! I miss sat morning hikes followed by breakfast (without having to cut anyone’s pancakes) I’m not sure what I would do if I drank an entire cup of coffee without having to reheat it….
Hope we win! 🙂
Date night? What is that?
We would like to try it!
A night out sans kids would be fabulous 🙂 Count me in!
how about if the husband and I stay home with some wine and the sitter takes the boys to see the spoonge bob movie?!?!?! 🙂
With four kids my husband and I do not get many date nights. I think a dinner out without little hands reaching into our food would be great! Thanks for the chance.
hi
This is fantastic. I’m in! I mean, I’m going out!
I would love a night out with my guy. Actually getting to have a real, uninterrupted conversation, what a concept!
It has been a few months since we went out on a date without children. It was our baby free night before I gave birth to our second princess. Before that it had been about 2 years. I think it’s important to do it more often than we have been able too. We enjoy the regular dinner and a movie but we also love glow bowling! I think any sitter is a hero for giving mommy and daddy some much needed date night time.
I would LOVE the chance to go on a date! Except for once a year on our anniversary we really don’t have any kids free time. It would be so nice to reconnect… And maybe remember why we even liked each other! Lol! I would want to do something fun and slightly competitive… Maybe miniature golfing or bowling.
As a babysitter in the past I always loved it when my families let me “break the rules” with a special show or movie or by playing a “trick” on the parents and putting the kids to bed in the wrong room! We really dont often have babysitters but I think Id have her help them make a blanket fort. They wouldn’t be able to say goodbye fast enough then!! 😉
i never have the chance to go on a date we work separate hours but i would love to go to dinner
I would love to do dinner and a movie with my wife for sure. thankyou, ken
Last time we went out alone together was when I was 9 months pregnant 14 years ago.
Thanks so much to all who entered. Congrats to Connie, Nicole, Lori, Aimee H, and new email subscriber Tanya. Random.org chose these 5 lucky winners. I’ll be in touch via email!
I need this service! It’s so hard to find any me-time.