A Great Way to Book Babysitters

We’re often scrambling to find sitters for date nights. It can be tough to find someone who’s available on weekends, and texting a bunch of different sitters (and waiting for their replies) can take ages, so…

Recently we tried Date Night Now, the new on-demand service from Sittercity. The Date Night Now website helps you easily find a sitter for a Thursday to Sunday night. Before booking, you can view each sitter’s experience and even watch video interviews. All sitters have gone through extensive screening and background checks, and you can read reviews from other parents.

A couple weekends ago, we booked Sheila. She arrived right on time and was lovely and playful. Anton, who tends to be very shy, warmed right up to her and showed her all of his favorite toys—bus, taxi, guitar and basketball—and didn’t even notice when we left! (That’s unprecedented.)

Date Night Now is a lifesaver for busy parents. There are no subscription fees, and I was really impressed by the caliber of their sitters online. (And you can book your favorite sitters again and again.) Another big bonus was paying online; Alex and I are usually hunting for cash after getting home from dinner, but with Date Night Now, your sitter just records her total hours and you get an email with your receipt. So. Easy.

Sittercity is available around the country, and Date Night Now is available in Chicago and New York, with other cities coming soon.
Bonus: Date Night Now is offering all first-time users a FREE night of babysitting—up to four hours—using the code CUPOFJOCHI (for Chicago) or CUPOFJONYC (for Manhattan and Brooklyn). For real! Can you believe it? Please enjoy! Thanks so much!

(This post is sponsored by Date Night Now, a service we’re so glad to have discovered. Thank you for supporting the brands that support Cup of Jo)

  1. Wish we had this in Atlanta! Such a pain to have to pay a subscription service to get a sitter, so I love anything that doesn’t require a membership.


  2. We used sittercity to find our nanny, who’s been with us for 18 months + and also to find an evening baby-sitter. We did meet and interview our evening sitter before leaving her with our toddler, but I think that Date Night Now could be a great service, especially for people who only need occasional help.

    I think it’s important to remember that most people are good people, and that the vast majority of people on these websites would do a great job caring for them. Of course we should all be careful and following your gut instincts is important, but I think there is a way to balance caution with a positive outlook on life – and that’s something I want to model for my kids.

  3. I used urbansitters for a trip to NYC last year – our sitter was absolutely awesome, totally business-like and reassuring us to go out and have fun. Totally recommend.

  4. While in theory I like the idea of finding a sitter so quickly via the web (and I do find initially sitters that way, but not for same-day work), I need to try out my sitters and get to know them, check their references, watch them in action, etc, before I’d leave them alone for a date (or leave them alone in the daytime). Our kids are so young (going on 5 and 2), and won’t stay that way for long, and we are so fortunate to have them, we don’t mind staying in. Also, they couldn’t report to us any misbehavior, whether the sitter was having friends over, was glued to her phone, etc, etc. My husband and I do at-home after-hours date nights. Maybe later on, we will go out at night again, but only if we have known sitters. Sadly, in the case of abuse, it is more usual that the victim knows the abuser, who is a relative or friend of the family. When our kids were younger, we offered to friends with similarly little kids babysitting services (my husband could stay home with our kids while I watched the other kids). But this did not happen much as everyone was exhausted!

  5. What about friends? When I was raising my boys, I had a group of about six other moms with 1-2 kids each. We’d arrange date breakfasts, day outings, or evening events by asking one of the families to take our kids for X hours. Sometimes it would be a sleepover. Then we would owe them X hours in return. It was not complicated, this was pre-cell phone, and the kids all had a ball. And we geared up for our sitting nights with fun kid dinners and activities and enjoyed the chaos.

  6. I agree with the others who think this is unsafe. I’m sure there are tons of really great, reliable sitters on this site, but the thought of leaving my children with a stranger is terrifying.

  7. Cool service. Anton looks so darn charming. We’ve hit the jackpot with our sitter – I believe in hiring 13 and 14 year olds and training them for their first job when they’re still cheap :) since we don’t have babies. Our current sitter is available anytime we want – she’s never said no.

  8. Jo says...

    Thanks so much, Joanna! This is SO great to know. I’m going to spread the word to my friends in the city. (Too bad we’re from Northern NJ!)

  9. @Christie: Can’t say I blame you. Sorry to hear about what happened to you. My mom never let us be babysat by strangers, either. It was tough because we didn’t really know anyone (we had recently moved to a new country when I was a baby). As such, my parents never had any alone time. I always thought they were uber paranoid. I don’t have a kid yet, but the worry I am sure will always be in the back of my mind. On one hand I feel like it’s important to have alone/couple time and it’s reasonable to rely on babysitters (especially if you don’t have people you know in the city you live in), but on the other hand, I suppose it’s possible that they’re bad news. I like the idea of this service (like I said in my previous comment) but you’re right, it’s important to ensure the person is trustworthy, and that’s hard to do with someone you just met.

  10. I actually like this idea. I don’t have a kid yet, and I live in a Canadian city so it’s not like something like this will come here… probably ever… but it’s a cool concept.

  11. Oh hell no. No way I would do this to find someone to watch my kids. A background check doesn’t show everything, like past hospitalization a for mental health problems. I was sexually abused by a sitter as a child. I only choose people known to me or others to stay with my kids. I would rather skip the date then do this.

  12. I was a babysitter with Sittercity in Portland, Oregon for about a year a half (during 2011-2012), and that combined with being an office temp for a great agency, was a solution for me to stay flexible and enjoy a variety of jobs before moving oversees for a while (while also preparing to get married and then have my own baby and now another on the way). Sittercity was great for me. I ended cultivating a consistent relationship with five families, each with kids of different ages. It ended up being being a very meaningful experience, as it prepared me for having my own kids. I got to preview and experience different techniques across a spectrum – making baby food versus store bought, cloth diapers versus disposable, kinds of schedules, parenting styles, bed times, bed time routines, amount of toys, books, etc.

    I hadn’t heard of Date Night Now but was happy to see that it is associated with Sittercity. I used to do on-call, last minute jobs through Sittercity when people would come into town and wanted to go out while I watched their baby in a hotel room. This reminded me of that somewhat. It was all very fun. That said, as one mother put it, it does require a lot of trust. It might not be for all parents, but when it works, Sittercity is a well-developed tool. I thought I would give the sitter perspective a bit, in case it would be of interest to anyone.

  13. I SO wish we had this in Portland! Finding a great sitter is so hard!

  14. This sounds great! I hope this is coming to Portland soon!!

  15. I’m psyched to try this, thanks for the code! We live in Chicago and I went to college with the founder of Sittercity, but had never heard of this service until now.

  16. These pictures are absolutely precious. I hope Date Night Now comes to San Francisco soon. We have other similar companies but I haven’t found any sitters that stick with me yet.

  17. I’m a sitter on Care.com in NYC AND SIttercity.com so it’s awesome you mentioned sittercity! Yes Venmo and Square apps are so great for paying as well as cash haha. Might have to apply to be a sitter for this new website! Thanks for the recommendation.

  18. I’m going to tell my daughter about this. She’s 24, living in Manhattan and adores kids. She was never sure how to go about finding someone who needed a babysitter :)

  19. FYI – you can pay friends (or sitters) via PayPal, Venmo, or Google Wallet (my favorite). I never have cash and it’s more convenient. Square charges a percentage, I believe.

  20. oh wow – thanks for the free night of babysitting – i’ll definitely be taking you up on this!

  21. This looks awesome!

    We already have a regular sitter, but I just wanted to say that having her come got SO much easier once we gave her a Square and she signed up for a Square account, so that we could pay her via credit card at the end of each night instead of having to add in an ATM trip at the end of our date. It ended up giving us an extra 5-10 min that we now spend chatting with her to catch up on how the night went!

  22. oh yay it’s the babysitters club in the digital age!

  23. They need to be in San Diego ASAP! That sounds like a great service.