Two Calendars, One Deal: How a Pro and a Student Made Time Work

The first few times I tried dating a younger man, it was just short of a disaster. At the time, I was publishing a book, and all that comes with it (revisions, book tours, media interviews, photoshoots, etc.) And my younger guys, whom I had met on dating apps, were either just finishing up their undergrad or had recently graduated. I was attracted to them because I really didn’t have time for a serious relationship, and I knew that men my age were often off-put by someone like me: you know, successful, independent, opinionated, or as one ex put it, “demanding.”

Anyway, one of my gal friends, also a high-powered woman in business, told me that she had recently started sugar dating, and the experience was completely different from being on the dating apps. She said that since there was an explicit understanding of mutual care, she felt that her partners were a lot more attentive and serious, without, of course, wanting something formal or traditional.

I was very hesitant at first, especially because my book was getting some buzz and I knew that I would be in the public eye, if not all over, then at least in my city. To be fair, it wasn’t set to be a Times Best Seller, but I also didn’t want to jeopardize my public image before my writing career even took off. But, my friend assured me that if I took my time to find someone responsible, there was absolutely nothing to worry about; other than, she joked, not falling in love with the guy.

So, I started my search. And I have to say that I was quite picky. I wanted someone driven but not so ambitious that they might sell me out to some journalist. I wanted someone interesting and open-minded. I wanted a guy who would respect women but not walk on eggshells around me. And I ended up finding all of that in a very cute package when I met Andy.

Andy was in his first year of an MFA program for writing. And that at first made me weary, thinking maybe he was only with me because he wanted a contact in the writing world. But our first date put me 100% at ease. He made it clear that he didn’t want professional help or even advice, but rather a little bit of financial support so that he could use his free time writing instead of working a minimum wage job. He seemed genuine and sweet, and thanks to his teaching assistant job, tutoring schedule, classload, and personal hobbies, as busy as I was.

Once I found out that we had chemistry and that I could trust him, it was time to iron out the details. I had been in enough failed relationships with younger men in the past to know that I couldn’t just hope that he was going to step up to the plate in the way that I needed him. So, I presented him with my list of, well, I call them guidelines, but maybe someone might call them demands:

A shared calendar

I live my life on Google Calendar. I use it to keep track of appointments, remember birthdays, my monthly cycle, personal tasks, everything. So, even though some of my friends kind of balked at the idea (“You would give him access to all of that personal information about yourself??”), It just made sense that we would share calendars. That way, we wouldn’t have to go back and forth a million times over text asking, “Are you free this day? No? How about this day?” Instead, we looked at each other’s calendars and then proposed date ideas for the days that we had free. Simple.

A protocol for rescheduling

One of my pet peeves is being stood up. And yes, I consider being stood up to include rescheduling or cancelling a date with a warning. From my perspective, if I had blocked that time out in advance, it’s a waste of that time, even if you give me a warning, because there’s usually not enough notice to schedule something else. Plus, changing plans kind of ruins my mood.

And yes, I know that to a certain point, that’s totally unreasonable. People get sick. They have fender benders. Things come up. I understand. That’s why I have a protocol:

• The earlier you let me know, the better, so that we can try rescheduling it within the same week.
• Within 48 hours of the date, the date will be canceled and allowance withheld for that week.
• And if it happens more than three times, sorry, but this just isn’t going to work for me.

Maybe it seems harsh, but in my experience, it’s better to have a system in place so that I’m not just building resentment.

A non-negotiable list

In my experience, a lack of goals paired with two busy lifestyles translates to a very unreliable relationship. Before you know it, months have passed, and you’ve barely sent each other a few half-hearted “so when are you free this week” texts. So, I like to go in with actionable goals, such as:

• One phone call per week, under 30 minutes
• One written check-in per week
• Two in-person (overnight) dates per month
• One weekend getaway per quarter

When you think about it, the non-negotiables aren’t unreasonable. It translates to under an hour of commitment a week, plus the in-person dates. And, having it all laid out in a way that feels a little bit like a college class syllabus just makes sense for two detail-oriented people like us.

Advanced notice for travel

Like I said, I expect one weekend getaway per quarter, and I make sure to plan it all out with Andy in the first week of the quarter. This usually looks like me sending him a few emails of places that we could go, as well as dates that would be ideal for me. As soon as I have the location and the dates squared away with him, I allow my personal assistant to book the accommodations and plane tickets and add everything to the shared calendar.

Not only does it make sense on a practical level, but it also gives the two of us something to look forward to throughout the quarter. We haven’t missed a getaway yet, and I think it’s an important opportunity for us both to destress.

Ongoing negotiations

The best way for an agreement like the one that Andy and I have to work over time is that it’s open to change. For example, there was one month in which Andy knew that he was going to be way too swamped for even a weekly call. So, for that month only, I arranged for him to come have dinner at my house, which is only a twenty-minute drive from his apartment, once a week. I always called a car for him so that he could spend that commute time working on his laptop in the back (thank goodness he doesn’t suffer from motion sickness) or, better yet, take a little catnap. Dinner was on the table waiting by the time he arrived. And, within forty-five minutes, we were done with the main course and dessert, and he headed back home.

It was a little bit more work for me than a phone call, sure, but I preferred it to not seeing or hearing from him for the whole month. And he admitted that it helped him stay fed and gave him a little bit of time to disconnect and unwind.

Andy is graduating next year, and I’ll be starting another book, so I know that this openness to change and adaptation is going to be essential for us. But I’m happy to say that we’re both committed to finding time for this relationship regardless of our busy schedules. And it’s that commitment, plus a borderline obsessive desire for organization, that makes it possible.