Finding it Hard To Fit In: The World of Today's Midlife Singles

05/05/2016 11:25 am ET Updated May 06, 2017

As Generation-X-ers and some of us younger Baby Boomers now share the real estate commonly called "midlife," the traditional notions about being single seem to have changed significantly since our 20's. In 2014, The Bureau of Labor Statistics reported that "single people now outnumbered married people." The world of dating and the seemingly impossible task of finding love has become a terrifying job of navigating in a digital jungle. Twenty or thirty-somethings are definitely comfortable socializing online, "liking," texting and typing many of their interactions. For some of us who started dating before the Internet, besides causing big headaches, these cyber searches and digital connections can feel like unnatural ways to begin a relationship.

Online dating sites do offer a perceived level of filtering until friends start retelling online dating horror stories. Some prefer online dating to having friends or family set them up because they feel they can better discern for themselves who is suitable company for a first date. This may be the biggest difference between dating at midlife and dating at 20 or 30: Discernment. It's not that we don't want to date and have fun. It's just we, mid-lifers, tend to be a little more selective about how and with whom we spend our time. Often, binge-watching with a bottle of Pinot Grigio wins out with me.

One alternative is organized events where people actually go to a venue to meet up with other singles. These events are usually organized for singles of specific age groups, which generally makes people feel more welcome. This is one reason I developed Introductions by Diana (IBD), which caters specifically to discerning Boston area singles age 45 and up. One of IBD's offerings is Dating Over Dinner events, where singles head out on the town for an elegant evening with like-minded people. Diana, the host of the events, properly introduces everyone at the event. It's a new take on a more traditional way of meeting people.

Over the years, I have met many midlife singles at my events and the overwhelming response to being at this kind of event is: "there is nothing else out there like it." It gives guests a much-needed opportunity to meet other midlife singles. One guest recounted his experience with online dating and said he wished that people posted current pictures and actually looked like what "they were selling." Similarly, another guest told me exactly why he chose IBD over online options: he could be introduced to single women in person, shake their hand and instantly get a sense of physical chemistry. It's clear that the in-real-life approach to meeting people still has very clear advantages, it just isn't the current popular method.

The unique format of IBD may just become a new modern tradition. For Generation X and Baby Boomers tired of today's digital options, events like these can have a more desirous appeal and a more personal touch. We'll see if it sticks as younger singles mature and they start to look up from their screens for new alternatives.

Read more from Dianne at Introductions by Diana.