Single Dad Dating

We hadn’t been dating that long, maybe two months, but we went ahead and set up a shared Google calendar. Between her parenting schedule and mine, we needed a little logistical help to find times we could actually see each other. It worked, and we both fell for each other a little more through our shared appreciation of planning ahead.

Sharing a Google calendar… just one of many aspects of dating as a single dad that my 20-year-old self wouldn’t have understood.

I started dating Emily in May 2016. She’s creative, compassionate, fascinating, beautiful,  intelligent, hard-working, a wonderful mom, and a woman of faith. And she’s going to be my wife! We got engaged this September, and we’re busy planning a winter wedding. We’re also planning to blend our families. We’re both single parents, and between us we have four kids, ages 3, 6, 9, and 14.

There’s a lot to look forward to, but in this blog post, I want to look back a little, and reflect on dating as a single parent. It’s… more complex than dating without kids.

There’s the Google calendar, which only got more useful as we saw more of each other. And there are the babysitters. I didn’t need those when dating back in college. I’ve got a great babysitter, who helped me out several times last summer. Emily was very appreciative of me going to the trouble to get a sitter so we could see each other. Once we got our parenting schedules better synced, I didn’t need sitters as often. We just scheduled our dates for nights we didn’t have our kids. It was a new version of my binary life. Some nights it was me and my kids; other nights I went out with my sweetheart.

That changed, of course, once our kids got involved. Now, sometimes it’s the two of us, sometimes the six of us, sometimes just four of us, all depending on our parenting scheduled. We took our time bringing our kids into the relationship, wanting to be very careful with the four precious hearts we loved so much. She didn’t meet my kids until we had been together about five months, and I met her kids a little after that. And our kids didn’t meet each other until we had been together almost a year. We talked about those meetings for a long time before they happened, making sure that we were ready, that our kids were ready, that we felt things between us were some kind of permanent, and that we knew how we wanted those first meetings to go. That intentional relationship building continues today, as we find times for the six of us to be together. We’ve been to Cheekwood, we’ve had backyard Easter egg hunts, we’ve gone camping, we’ve played freeze tag in the living room. It’s been good.

Pacing things for the kids has been important. Our family and friends have had their own paces, too. Finding a pace that worked for us, as well as our kids, and our family… that took some figuring out. What parts of holiday family gatherings are boyfriend appropriate? When should my kids meet her parents? How much time should I spend with her nieces and nephews? How can I get my girlfriend to meet my sibling who lives in Texas given the constraints of our parenting schedules? (I found myself introducing Emily to old friends, to help her know me, in part because my family was so far away.) Some of these questions we would have had even without kids, of course, and some of the pacing was more because of our divorces than our parenting status. But navigating these questions with kids took some careful thought.

Sometimes, it was friends and coworkers who weren’t sure what was happening. We live in the land of married-with-kids, and married people, understandably, don’t really get what it’s like to be dating in your 30s or 40s. (For instance, are +1s welcome at an event? That’s not always clear from the invitation.)  Strangers are the funniest, however. We were sitting on a bench outside a movie theater last summer, apparently looking like we were in love. This couple walks by with their child. The guy notices us and says, “That [points at his kid] is where all that [points at us] leads.” Um, thanks, dude. Little did he know that we have four kids between us.

That’s happened more than once, where someone sees us out on a date and assumes we don’t have kids. Maybe married people don’t look quite so much like teenagers when they’re out? I can’t describe how much fun it’s been to date Emily, and how rewarding it’s been to pursue her so intentionally. I love to ask her out, and she loves to be asked out. From the beginning, I was careful to plan dates where we would talk and interact and learn about each other. We didn’t go see a movie until our ninth date, and that movie was an independent film with subtitles about refugees that we discussed for an hour at Starbucks afterward! It’s been amazing to just be myself with her, doing and talking about the things that I like, and to find that she likes those things, too. I remember one phone call when I told her that there was a street art exhibit I wanted to see at a Nashville gallery.

Me: “They have a Banksy.”

Her: “No way!”

We get each other. And we have a strong dating game. I’m committed to maintaining that after we’re married!

Something else I don’t want to take for granted when we’re married: Getting to see each other every day. These days, Emily and I see each other almost every day, even if that involves a bit of driving (thankfully, she only lives 30 minutes away) or a lunch date on a work day. But before our kids met, we would go 4 or 5 days without seeing each other sometimes. Epic phone calls helped. I think our record was three hours, which is impressive when you realize it started after our kids went to bed. But those were long stretches. I’m looking forward to the time when, even on our busiest days, we’ll still get to see each other while we brush our teeth at night.

Social media helped with that time apart, too, although that took some figuring out. When do you start following your significant other online? We started with Instagram, I think because we both love photography and using photography to document our lives. Next came Twitter. I’m more active there than she is, but she uses it for her work a lot. I follow her work account, knowing that it’s her posting! Last came Facebook. In fact, it was a running joke for us that we had been dating so long but weren’t Facebook friends. It was six months before that happened! And it was some time after that before we posted pictures of each other there. (We take great selfies.) One reason we waited is that Facebook brings a lifetime of friends and family with it, and we wanted to meet more of those people in person before Facebook introduced us.

It’s really fun to be with someone as savvy about social media as Emily is. We send each other Instagram posts about travel and art and design all the time. We share tips for using social media effectively in our jobs. She gets my thing about not posting photos of my kids online. (Lately I’ve been reconsidering that rule, however, since I would really like to share some photos of the six of us on our adventures! Again, we take great selfies.) And she’s been incredibly helpful as I help my 14-year-old go online and navigate social media. I always smile when I see that she’s favorited one of Emily’s Instagram posts or vice versa!

My church life has changed a lot in the last year, too. I had been at Rolling Hills for twelve years, and it was the only church my daughters knew. I had been looking for a new place for a little while before I met Emily. Her church, Otter Creek, is now my church, and it’s a great fit. I get so much out of the classes and services. Moving the girls has been challenging, especially since they’re only with me two Sundays a month to make friends and build relationships at the new church. But I’m thankful that Emily and I have an incredible small group at Otter Creek… families who invest in each other and pray for each other, families that adopt and foster, families that blend like ours. They’ve made me feel very welcome at my new church, and it’s been fun to make new friends and build new relationships. Emily has been going to Otter Creek for several years, and she knows lots of people there!

That points to another aspect of dating at this stage of life: We both have very full lives, with lots of backstory. Getting to know each other, our friends, our families, our kids, our stories, our woundings… it’s been an exciting, beautiful, and sometimes hard process. We shared the short versions of our divorce stories, then the medium versions, and then the long versions. (That was a very late night.) I’ve learned a lot about myself, things that I thought I had figured out after my divorce but hadn’t been tested. I’ve learned so much about Emily, about our relationship, and about love. We’ve met each other with honesty and bravery and compassion, and we’ve pursued each other intentionally and with much prayer. I’m thankful that she knows me so well and loves me so much. She’s a blessing to me and my kids, and I love spending time with her and her kids. I’m so excited to explore the world with her and to call her my wife.

I know that our shared Google calendar will always be full!