How to Manage Your Dating Connections Like a Boss
Dating is about meeting people, and just like your work or social life, you can level up your game. It’s time to get organized.
Once upon a time years ago, I could not, for the life of me, remember my approaching date’s name or anything about him. On a blind date, this doesn’t matter all that much. For someone you’ve exchanged a multitude of conversations with, this is a tad unforgivable.
I went through the entire date trying to piece things together, distracted by my own confusion, surreptitiously scanning my phone when he went to the bathroom to no avail. Still unable to figure out where the profile was and on which app, I even started to doubt the originality of the things I was saying to him, as if he knew I’d confused him with another profile. It felt like a magical disappearing act had taken over my brain and my phone.
Never again would I disrespect someone’s time like that. I resolved to tap into my organizer skills, stat.
Funny enough, after years of conversations with singles, it turns out this is a really common problem and it’s only getting worse as social platforms of all kinds expand and compete. Our time with these platforms and our ability to use them wisely and in an organized fashion is really friggin’ challenging.
And it’s not just daters suffering with disorganization, platform overload, and time wasting.
Recently, at a weekend event with a very large handful of business students, it became clear to me that even the most organized people in the world are having trouble with wasted time, remembering where they met, agreeing which platforms to stay connected on, how to maintain social groups, and where to store information and conversations. Did you send that on WhatsApp or facebook? Did we meet on LinkedIn or Zoom? Oh, you commented on that Instagram story and then we met at that mixer and you introduced me to your friend who’s in the Slack channel I was talking about on the Tech Nerd workspace, that’s right.
These were management students. Any group of intergenerational nuance will face this issue even more dramatically. We need to start streamlining. There are tools for this.
Whenever I get to pull tips from my business life and transpose them to the singles out there, some feisty little power suit Cupid angel gets their wings, I’m pretty damn sure.
Dating, and any other form of personal connection, generally runs smoother if you can save stuff, remember stuff, find stuff, and do so quickly and with ease. Our digital lives are only getting more integrated into our web of relationships, and managing time and contacts is starting to feel like forgetting which streaming platform you watched that one show on — was it Netflix? Naw, had to be HBO. 30 minutes later… that’s right, Hulu.
It’s a lot. We need help. Here are some pro tips for organizing your contacts, your dating life, and your brain.
Time Management
Part of being a superb organizer is using time wisely. You must do this for your time on the platforms, your time organizing contacts, and the actual dates themselves.
Let’s talk about dates.
When it comes to time, how do we think about our value with strangers? It’s a tough one. I’ve written a bit about time and closeness. On one hand, you could say anyone who isn’t a serious dating prospect is a “waste of time”. That feels very right in hindsight but dating doesn’t work that way.
A little bit of time with the wrong stranger could be valuable in that it informs you of something you missed with initial interactions (i.e. our lifestyles are way further apart than I thought). It can also reveal something you realize you need to include in your desires going forward (i.e. turns out I really do need someone whose diet is very close to mine, whoops).
Even time with a perfectly nice stranger that you just don’t want to date can be valuable in understanding how their profile and interactions were reflected in real life. If you let it, that time could potentially increase your ability to read people and profiles better — which saves you future time. But be wise in how much you dedicate to that endeavor.
Overspending time on strangers before you get to know them in real life will lead to distress. Remember that virtual connections have a hard limit of closeness. You must assess the tradeoff between time spent virtually (including video dates) and in-person. In-person time is more informative and more valuable to you, but requires more effort, resources and trust.
My advice — don’t virtually message for more than a week before you plan a video or in-person date. Frankly, I generally set something up within a day of matching. Sometimes, within minutes. The best way to not waste your time is to get the ball rolling. This also lets you know immediately how serious someone really is. If they seem shy to actually set a date, cut your losses and move on.
If you like video dates, go on one or two with a good match before you meet in person. This uses less resources, is more flexible and much more safe, but you still have a great opportunity to get to know someone on a much more intimate level than messaging. #BossMove. Some people don’t like them, I get it. Remote zoom workers are so sick of their screen, they may want a break. If that’s the case, fine! It’s in-person date time!
I’m a huge advocate for brief, casual first dates where both folks pay for themselves or keep the tab cheap. Go on a walk, grab a refreshment somewhere or meet them at their dog park for a fun chat. Remember, in-person time is more informative. You can get a pretty quick grasp on someone with in-person time versus virtual. I haven’t always followed this first date advice, and sometimes it works out just fine doing a nice dinner or activity, but take the pressure off and just use date #1 as a meet-and-greet. There will be plenty of time for romance if you’re feelin’ it.
It may seem obvious, but do everything you can to be on time with any date. Time management has a lot to do with respect and showing someone you respect them by being on time is very sexy. Great — public service announcement, over.
After date #1, the road forks in many ways. I’d be foolish to give you too much general time management advice beyond date #1 and probably pretty hypocritical. Relationships blossom in all different time frames, attraction can grow or diminish, and life throws you curve balls all the time. Many good first dates go sour in dates #2 or #3 if it’s not meant to be. Some may last a few months and the others a lifetime. Time management after date #1 is hard to define, but the general rule of thumb is that if you really like each other, you will make time to see each other as often as you can within reason.
Now, on to the apps.
For anyone who has ever downloaded a dating app, you know time is a challenge from the moment you sign on. Building your own profile takes some effort and then profiles start falling from the sky like Tetris pieces needing to be reviewed, rotated and dropped into position before moving on, and why would you ever let that long hero piece fall by the wayside!? You were right about to clear four rows!
What happens? Profile review addiction. Many of us have suffered from zombie scrolling where minutes and hours are lost to the mindless scroll. At first you were young and in love with every other profile, reviewing it with care, noting details and making sure you saw every pic. 50 profiles in, you’re swiping before you even read their name. Messages get sloppier and your mood drops if there isn’t enough of a response for all your effort.
After a certain amount of time, reviewing profiles is not productive and no longer in the healthy zone. Get out. You’re wasting everyone’s time, including your own. This is now time better spent doing something to enhance your life in another way.
Profile review addiction is not helpful to maintaining quality connections or matching with people you actually want to date and that’s what you’re there for. To go all in with the business metaphor, how should you manage this “dating” project effectively? Where can you see that you are not using resources wisely? What would a good manager or boss do?
Give yourself a time limit for the day to review new profiles or matches with care and enthusiasm. Literally set a timer if you need to; I know how powerful Tetris can be. I’d say 30 minutes tops, but you do you.
During your profile review time, you might likely also have some new matches to review and messages to answer. Maybe, oh maybe, you even need to set up a few dates!
How then, can we best manage our time once we have some promising matches in the books?
Personal Contact Management with Bl@ckbook
There are plenty of contact management apps out there, but dating contacts can be different. You may not want to mingle all your “Angela (Bumble)” and “Adam (Hinge)” contacts with the rest of your digital rolodex. That’s fair.
If you don’t know it yet, download and start using Bl@ckbook, the up-and-coming match tracking and PCM (personal contact management) app that organizes your dates from all over.
The basic idea of Bl@ckbook is that you can manage profiles that you’ve matched with from all the different sites in one place and you have total control over what you add and how much info. Profiles can even be started just from a picture, so you can add folks that you meet in real life too.
Eliminating the toggle between app interfaces and the sifting through matches that were duds is a relief. After all, not every “like”, match or comment is going to be a date. With Bl@ckbook, you get to customize your winners all in one place, add the info you want to remember and delete them if you need to later on. Additionally, their profile and info won’t magically disappear if something goes wrong with the app of origin. Match tracking for the win!
What I like most about Bl@ckbook is that it can be specific to romantic interests only — and perhaps it’s nice to compartmentalize that social network for privacy — but it doesn’t have to be. That’s up to you.
This is quite literally the little black book of the digital age and it’s improving all the time.
Its female founder — aside from donating kidneys to strangers, winning world rowing events and sowing Covid-19 masks for hospitals — is passionate about eliminating awkward faux pas with new dating matches (ahem, guilty) and has pretty big goals in mind for future development. A few bugs are still being worked out, but this app has incredible potential — give it a whirl!
Okay, dating friends, it’s about that time… time to take your middle finger off the down arrow key and move on. But before you go…
This one was free! Liking the vibe? Interested in more dating tips? Looking for a dating coach? Check out You Can Date Better’s site for more resources and consider signing up to become a Medium member. It’s $5 a month, giving you unlimited access to stories on Medium. And hey, if you sign up using my link, I’ll earn a small commission. Sweet!
