Why Dating Can Feel So Damn Hard (And Why It’s Still Worth It)

Dating is tough. Period.

I know, because I’ve been there… through my 20s, 30s, and early 40s. From the outside, my life looked full. I had a solid career, close family ties, amazing friendships, and the means to travel and live adventurously. I bought my condo. I worked hard. I made big life moves and figured things out when challenges hit. I had so many pieces of the pie filled in.

Except for that one piece. The relationship piece. It kept overshadowing everything else.

I’d be fine most days, then I’d go to a wedding and find myself sitting alone during the slow songs, blinking back tears. Or I’d be at a concert, surrounded by dreaded “concert couples” (IYKYK), and suddenly feel the pang of being single all over again. All the fullness of my life felt eclipsed by what wasn’t there.

Here’s the truth: you can make dating happen. You can download the apps, go on dates, attend singles events, meet new people. What you can’t control is the outcome. You can’t make the right person appear. You can’t snap your fingers and be in the loving relationship you so desire. That’s what makes dating feel so frustrating and elusive, compared to all the other things in life that you can “make happen” if you put your mind to it and work hard. And that’s the part that made me feel powerless, frustrated, and sometimes downright hopeless.

I dated. A lot. I had several relationships that lasted 1-3 years. But deep down, I knew they weren’t the right fit. I even came to accept the possibility that I might never find my person, and could still have a meaningful, fulfilling life. I did have a meaningful, fulfilling life. That was freeing. But it didn’t erase the truth that I really, really wanted a long-term partnership. 

So, I kept going. I took breaks when I needed to. I worked on myself. I invested in the other relationships in my life—with friends, family, colleagues. And eventually, I found him. At 45.

Was it a long road? Absolutely. Was it worth it? Every bit.

And now, as a matchmaker and dating coach, I see those same struggles reflected back in the clients I work with. The no-shows. The “actually, I changed my mind” texts. The disappointment. The self-doubt. The emotional rollercoaster of hope and heartbreak. The scarcity mindset that whispers, All the good ones are taken.

If that’s where you are right now, I want you to know: I see you. I’ve been you. And while I can’t promise instant results, I can help you navigate dating with more clarity, more support, and more possibility.

Because love at the right time, with the right person, is possible.

Ready to take a different approach? Schedule an intro call with me to explore matchmaking or dating coaching.

Not quite ready for that step? Join my free singles database—it only takes a few minutes, and it’s one small but powerful way to open the door to future possibilities.

Don’t give up. Love is worth it.