The holiday season is fast approaching, a season of joy for some, and depression for others. One of the key problems: loneliness. Dating apps have evolved from merely swiping left/right. AI matchmaking elements have been added as product enhancements, and curious what the results will prove to be over time, as we’re not quite convinced that an algorithm is capable of understanding human emotions on a granular level, and isn’t love part of the equation when looking for a life mate? Yes, you can check all of the boxes, but what a person wants and what they need are often two quite different things, trust us.

We’ve introduced nearly two dozen couples over the years, who would never have met otherwise. In most cases, the parties rejected our choices after the first meeting, yet did indeed marry, in most cases due to in no small part to trickery on our part. We will also mention that none of the pairings ended in divorce. Superconnectors like Yours Truly assess things differently.

Here’s something else to consider: tis the season of holiday movies and holiday parties. As to the first, here’s Your Complete 2025 Holiday TV Schedule — Hallmark, Netflix, Disney+, Lifetime And More. Holiday films are primarily about people finding their life partners in unlikely places and under unlikely circumstances. Case in point: our favorite holiday movie, Die Hard.

Yes, Bruce Willis is fighting bad guys to save his estranged wife, with whom he is still in love, and – spoiler alert! -at the end of the day and the film, the hero prevails, saves the fair maiden, and ride off happily into that good night with the now reconciled love of his life. And Yippee Kaya to that! There is that ongoing debate as to whether Die Hard is a holiday movie. We will point out all of the Christmas paraphernalia and music playing throughout, what to speak of the fact that the hero’s wife’s name is – wait for it! – Holly!

Which brings us to our next point: holiday parties. They’re back in full force, and the invites are pouring in. Founders go to network, of course, as they should, whether or not they’re raising. It’s important to meet investors, potential mentors, partners or advisors, even before you may need them. It’s called ‘building relationships, and don’t forget those all-important follow up emails, etc., referencing where it was you met to refresh their memories.

But are founders et al missing the forest through the trees when attending these events? We have an investor friend who is single and uses dating apps, so far, to no avail, re finding that special someone. She attends events all the time. In post-event photos, she notices that she’s surrounded by men, some of whom she finds attractive, and some of whom she’d met at the event and was attracted to even then. Some have asked her out, but she’s there to network, she insists, so she politely declines.

Why are the missions mutually exclusive? Isn’t multitasking in the tech sector’s DNA? So what’s the problem and as for the preponderance of people who believe that their true love is hidden in the algorithm, we say to you, dating is a numbers game, but are you focusing on the wrong numbers? It’s time to cast your attention to the throngs who show up at networking events.

Why are the missions mutually exclusive? Isn’t multitasking in the tech sector’s DNA? So what’s the problem and with the preponderance of people who believe that their true love is hidden in the algorithm, we say to you, dating is a numbers game, but are you focusing on the wrong numbers?

Dating is never easy. It means putting yourself out there, but founders wouldn’t know anything about that, what, eh, considering that they’re doing the same each and every time they pitch to an investor. “Believe it or not, Boston College teaches a course in how to date, and there’s good advice here for singles of all ages,” writes American Magazine.

Something else happens to founders this time of year. With the holidays fast approaching, a time when investors tend to unplug/kick back a bit, a desperation sets in whereby founders feel they must get funding in/the round closed before investors check out. It can and does happen, but that’s more the exception than the rule. This is the time to cultivate relationships and prepare to come out strong when the new year arrives – a time for making a list and checking it twice, meaning, make sure the investors you met invest in your space, or it’s a waste of everyone’s time.

Speaking of loneliness and seasonal depression, depression may start in winter, but it’s a common misconception that “the days leading up to a major holiday like Thanksgiving or Christmas would seem to be peak suicide times,” says Psychology Today. “However, suicide rates are highest in the spring.” Which may be why T.S. Eliot, in The Waste Land, wrote that “April is the cruelest month.” With all of the parties going on this time of year, time to shake off those gloomy thoughts of possibly doing yourself in, which never really solves anything, and get out there and kill it! Onward and forward.