Criticised for using automated scheduling tools to organise catching up one-to-one with friends


For the last few years, I’ve been using automated scheduling tools, such as Calendly and to schedule catch-ups with friends. These aren’t business-related catch-ups; I just haven’t seen someone in a while and want to catch up with them over a beverage.

However, lately I’ve received some constructive criticism from some of my friends for this method of organising a time to meet. Have I just gone too far with automating various aspects of my life?


The following are a couple of reasons why people have criticised me for using these tools:

  • It comes across as impersonal.
  • I’m being selfish with my time by only having a few slots free (because I’m busy!)

Proposed Solution

Despite the constructive criticism I’ve received, I’d still love to use these scheduling tools due to the benefits outlined below. I’m thinking that I could provide the recipient of my one-to-one catch-up invitation with an easy way out. For example:

Hey …,

Would you like to catch up for coffee or lunch sometime soon?

You can see my free times at <insert_url_here>. You can also use this website to create a calendar appointment that will populate both of our calendars. However, if none of my free times suit, no stress - let me know what times you’re free, and I’ll see if I can move some of my existing appointments around :-).

Look forward to catching up soon!



As you can probably expect - given that we’re all automation nerds to some extent! - the benefits of using an automated scheduling tool are numerous. Here are two that immediately come to mind:

  • I don’t waste time going back and forth trying to find a date and time that suits.
    • In Digital Minimalism, Cal Newport outlines why we don’t get anywhere near the social satisfaction from written communication such as SMS or email compared with face-to-face communication (the irony of asking this question on here!). Consequently, I see using this communication to organise a time to meet as a waste of time, and I want to minimise the time I spend doing it.
  • Easy to organise multiple one-to-one catch-ups simultaneously.
    • Since the automated scheduling tool links to my calendar, when one timeslot is taken by one person, it automatically updates on the scheduling tool so that I don’t inadvertently double-book.
    • By contrast, if I contact five people separately around the same time with five free timeslots, the chance of two people booking the same time is (given a bunch of statistical assumptions) about 96% (1 - 5!/5^5). This just creates more work.

How about asking your friends to provide three times that work for them?
I think some back and forth isn’t so bad. It can also give you an idea of their current mental state based on subtleties of wording, etc. and also help re-establish the connection with them.

You can also set up your next visit at the end of your current visit, before leaving the coffee shop.

My friends and I have a standing meeting scheduled for every two weeks at the same time and place. We try to confirm the next meeting time before leaving, just to be sure there isn’t a conflict.


I have never used any digital communication with friends, I only use it for work, except to ask if they are free to receive a call (via text). For me, a 30 second phone call with an individual friend is always enough to arrange a meeting. I don’t tend to meet groups of friends because all my friends have kids and so do I, so most meetings are between families.

I would be quite offended if a friend didn’t just speak to me, using a platform is far too business oriented and impersonal. I guess it may be cultural: people in Spain also love talking on the phone. Most of my friends do not have social media and do not have chat apps on their phones except for iMessage, and they often take days to respond to a message. For me, a call is the way to go with anything social.

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Alright I’ll go a bit against the grain. Super cool automation, that said it comes across as a bit impersonal. I think the phrasing “I’ll see if I can move some of my existing appointments” throws me off. Now don’t get my wrong this automation is well intentioned. I like @JohnAtl’s thought of asking for three times or dates/days of the week that work best for them. I’m also open to hearing other thoughts at the expense of seeming too harsh.

I have a scheduled note that reminds me to get in touch with my family. Why? Because I get immersed in other business and easily loose track of time rather quickly.

I see no issue with the use of digital technology to do this. It replaces the manual sticky note on the calendar that we move a few days ahead after we call home from college.

What I see here as impersonal is the follow up that is done with a business-like form letter (and a calendar scheduling link to boot).

I suggest that YOU have to change YOUR mode of operation on this approach. Set the digital reminders. Then, pick up the phone and call. Or, take the time at that point to actually write an email that says something more than a form-letter email that you spam to your contacts at that point.

Otherwise, it really is you running your personal life as a business. From the outside looking in, I can see why your friends are offended.



I’ve never known these services to be used for personal contacts. I would probably suspect the email was a phishing scam and delete it.

I think a better flow for the conversation is to add another step:

You: Hey, it’s been a while! We should get together for…

Them (presumably): Sure! When should we…

You: (Ask them for three times, send them your free times, etc…)

This separates the message “I’d like to visit with you” from “I’m so busy. Here is when I’m available”, and establishes a mutual desire to get together before attempting to coordinate a time. This is a pattern that friends use, rather than one for maintaining a business (sales) relationship.

Edit to add: It’s (slightly) less autonomous, but that’s the point. Psychology is weird like that :slight_smile:

That is NOT wasting time, it is called connecting. Pick up the phone, talk a bit, get your calendars out, pick a date, decide where to go … connecting.


Caveat: I’m the Uncle who has his nieces’ and nephews’ birthdays on auto-bill-pay (it’s cash, they’re happy).
That said, I put more effort into maintaining personal relationships, and use a combination of the approaches mentioned above. Time with family and friends requires greater sensitivity to feelings and emotions than most business meetings. Plus, not everyone is as impressed with ninja geek skills as we are.

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Just wanted to say that this thread has finally prompted me to put reminders in Due to contact family members, though I do think automating reminders for me is fine, automating the messages is potentially impersonal. If you could throw in a range of 3-5 random messages so they aren’t the same every time, it could work though.

I’d be really annoyed to receive this if I were a personal acquaintance or friend. I get it, but the implication is that I’m bad at communicating with and you hadn’t the courage to tell me personally, and that I’m ‘worth’ exactly x minutes of your time and no more. Which is true on some level, but people don’t want to be confronted with that so starkly.

I’d vote for a mix of standing engagements (like the every couple of weeks example above) and using your reminders to efficiently call people on their birthday or something. :slight_smile:

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Also, every is different. If this works for you and you keep in touch with friends better, then so what if they think you’re a bit odd with your calendaring? It’s a tad mechanical, but not so bad.

In my circles though, everyone would find the online meetings thing a complete turn off and refuse to use it. If your friends are more used to those kinds of apps, then fine (our social things at work are organised in this way, when there are large groups. For small numbers it feels friendlier to try to chat it out).

In this day and age, I guess anything that gets people together face-to-face is useful. Only time will tell how your friends feel about this. On a side note, do you also send out a timed agenda before you meet?

I have a similar problem and use an automated solution. I personally feel it is kinder to both of us to have the scheduling automated, but there are a couple things I’ve tweaked for this very situation.

1 - I have a “top secret” event for friends-only that gives increased availability and longer meeting times. It also has the phrase top-secret in the url (now that I’m thinking about it, “friends-only” might be a better phrase. Most people know that these times are more ample than the default scheduling of meetings I have for strangers/students on my website.

2 - The language I use is typically something like: I’m using the Calendly service in an effort to shorten the back and forth nature of trying to find “a time that works” for the both of us. Doing so gives you the ability and control to cancel or reschedule without having to contact me. Please accept my apologies for the impersonal and tech-oriented nature of what should be more casual and personal experience. I’d much rather just pop over.

3 - There are certain friends (either bc of their nature or the nature of our friendship) that I wouldn’t use this for and I’d never use it for family.

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I like “top secret”, for what it’s worth. Seems like a fun way of saying friends only!

One takeaway from this discussion: if a relationship is personal, people expect a little more effort for you to participate.

“Business” relationships have clear purposes and outcomes for those involved. As such who has to do what is typically clear, and it doesn’t matter as long as the work gets done.

Personal relationships are not so objective. The point is to put effort into maintaining them. It shows that the effort is worth it—that you care.
Automating this is a signal that the relationship isn’t worth the effort. Can you automate caring? Perhaps not without removing the caring part.

Maybe this is why I have no friends. :upside_down_face:

A tangent: the back-end management of personal relationships is something that can be automated without anyone ever knowing. Apps like UpHabit promise to act as personal CRMs. I didn’t like UpHabit too much so I’d love some other suggestions on this front!

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Even with clients, I make it personal first. So, for example, if we’re corresponding by email and setting up a meeting or phone call, I’ll suggest a few dates, then say something like, “If those don’t work, I can send more, or you can send me some that work for you. Or, if it’s easier for you, you can get direct access to my calendar to select a date here: [link to booking page].” I find that about 70% of the time, they go to the link.


I was thinking along these lines too, eg meet a friend more naturally/traditionally/personally, then at that meeting bring up the more automated system idea and see how it goes.