How to Survive the First Vacation with the Boyfriend AND the Kids

Every single mom, when she begins to date, hopes to find a guy who will love her children as much as he loves her. She knows she comes with baggage – both in the form of a failed marriage or relationship and in the form of a talkative, precocious, amazing child or two. If she’s lucky, she finds someone who will take the whole package and try his best to slide into her family in the sometimes awkward role of “Mom’s Boyfriend”.

I’m writing this from the ninth floor of the Hilton in San Francisco while my two children share a double bed behind me. Their cheeks are rosy from a hot bath after a day walking miles across the City by the Bay. I’m waiting for my boyfriend to arrive with a stiff vodka cranberry which will do more to ease the ache in my feet and legs than just a hot bath and I’m scrolling through the pictures of our day wandering the city.


Having just vacationed with my ex and his family, it’s difficult not to note the differences between the experiences. While Disneyland with my in-laws was fantastic and my ex was fine minus the idiosyncrasies that make him my ex, this trip with my current boyfriend has been more relaxed, if a bit bumpier.

My ex and I have traveled extensively together. We have our routine down pat, from packing to checking in to how we like to explore an area, we were a finely tuned team. We fell into that routine on our most recent vacation with the kids with barely a bump.

My current boyfriend and I have never traveled together making this vacation a trial by fire. After all, even my ex and I fray at the edges when it comes to traveling with children. In hindsight, it might have been nice to take a vacation together before adding a preschooler and a seven-year-old to the mix.

I have to give the guy credit. He’s taking it in stride, the whining four-year-old who doesn’t want to walk up one more hill and the lobster ravioli eating seven-year-old who asks for seconds. He knows my children fairly well and is great with them. But we haven’t yet developed our team. We’re still learning about each other and the things that make us tick, both while vacationing and while at home.

Still, there are moments, such as when we were watching a street performer juggle fire and my son leaned back against my boyfriend to point out how high the sticks were flying and my daughter crawled up into my lap to clap and cheer, that I think how nice it is to have this man with me to share these experiences.