Dating difficulties? Here’s what I’ve learned

By Owen Devlin April 1, 2026 Two words come to mind that accurately articulate my feelings about my dating experiences in Boston. Relationships in Boston are endlessly hopeless and infuriating. And dating apps only make these emotions worse. I was initially apprehensive – and too eagerly optimistic – about the idea of creating a profile on every popular dating app. But now I regret it. I was under the impression that joining an app would be the answer to my single woes. All I’d need to do was swipe to find the one. I’d have to sacrifice my attempts to meet someone organically so long as I’d be scooped up the next day. And the rest would be history. I’ve always considered myself a hopeless romantic and have deeply appreciated the art of a true love story. When I watch a romance movie, I like to immerse myself in the lives of the characters – as if they’re real people – to empathize with their experiences. But I have one condition. I only watch films with storybook endings, which is why I adore “Purple Hearts” and “Can’t Hardly Wait.” And I also believe it’s because these films help me get further transfixed on keeping my fairytale – and quite frankly – unrealistic romance fantasy alive in my head. Or maybe it’s because I still embrace meeting someone the old fashioned way – through a good chat. These films create the illusion that finding the ideal partner is easy and that it’s guaranteed to happen through a series of serendipitous events carefully arranged to depict something real – including the all-too-familiar coffee spill scene – found in most Hallmark movies. One person is running late for work and just happens to bump into – quite literally – the love of their life. And the notorious freeze frame camera shot where the two are lost in a trance realizing they’re soulmates. But these examples can’t be farther from the truth. One of the many drawbacks of dating apps is that they utilize an algorithm that’s intentionally designed to bring people together based on location, profile similarities and mutual interests as opposed to creating features that enhance individual personalities. Answering voice prompts and embedding seconds-long videos into a Hinge profile isn’t enough. But it’s not just the apps. It’s users that aren’t honest about their intentions, aren’t consistent with communication and talks that don’t go anywhere. And dating apps perpetuate the phenomenon – and continuous patterns – of ghosting. And we all recognize how devastating, defeating and confusing that can be. I can’t tell you how many times I’ve identified potential, but the other person stops all contact, doesn’t respond as frequently or doesn’t respond with the same level of enthusiasm. That’s a red flag in my book. And unfortunately, the so-called tell-tale dating signs – like maintaining eye contact, leaning and smiling – aren’t always the best indicators. I went on a date earlier this year, and the signals were there, but it ultimately wasn’t meant to be. I’ve talked with many people who’ve expressed similar frustrations around dating apps, but a few of my close family members found love this way. It took time, but they found their matches. So, I have to believe there’s hope. And my optimism is a testament to that. Here’s the mindset I’ve adapted throughout the process. Dating isn’t a bottomless pit of rejection. If you think you’ve done something wrong, you haven’t. And when a person abruptly ends contact, it doesn’t mean they’re rejecting you as a person. Life happens. Earlier I said that I thought finding a partner would be instantaneous after joining apps. I was wrong. There’s never a right time to meet someone, and you can never be fully prepared when it happens. You’ll meet someone when you aren’t thinking about it. Take one day at a time, partake in hobbies that bring joy and let your journey unfold. Drop a comment below with your thoughts about dating in Boston! I'd love to start an open dialogue!