It just took me 7 years to ask her out

How did you meet your significant other?

If you’ve been reading this blog for the last two months, you’ve heard me talk about Sierra. And if you’ve been reading this blog for the last two months, you probably already know the story bit by bit. But since the prompt is asking for it, and I feel like telling the story again—and this is my blog and I can do what I want to—here goes.

Simply put, the emergence, or return if you will, of Sierra is the most startling new development in my life in a very long time.

The Seven-Year Itch (Minus the Itch)

To the best of my recollection, it was the late summer or early fall of 2019. X2 and I had been broken up for a little over a year. I was dating other people and still on the apps, which is where I initially met Sierra. We chatted for a bit, mostly through the app, though I think we briefly traded phone numbers. I remember thinking she was really cool, but I wasn’t getting much of a vibe that she was interested in me.

However, Sierra herself recently told me that from what she recalls, I was complaining a lot about X2 at that point—specifically regarding parenting time and things of that sort. As I’m writing this, it has occurred to me that maybe she wasn’t ignoring me because she wasn’t interested. Maybe I was just bitching about my ex. Which, in hindsight, I totally understand.

Because I wasn’t getting that vibe, I started looking elsewhere. Shortly after that, I ended up getting back together with X2 for our last six-month run—a period I’ve described on numerous occasions as being just long enough to remember why we broke up in the first place.

Even after that final split, X2 held some kind of invisible grip on me for a long time—something I agonized over for nearly a year. I eventually realized that because of my first divorce, I had become more committed to making the relationship work than I was actually compatible with X2 herself. I felt like I couldn’t fail again. And while I was white-knuckling that belief, the relationship was just falling apart around us.

X2 and I broke up for good just before the COVID lockdowns began in late winter/early spring 2020. Around that same time, Sierra met another guy, whom she was with for nearly five years.

At some point, Sierra and I became friends on Instagram and Facebook. As she phrased it to me the other night, “You kind of tracked me down”—which, yes, fair enough, I was keeping an eye out for her. We kept it very casual, almost neighbor-like. We shared political posts and occasionally liked updates about each other’s kids. After a while, though, I got sick of seeing photos of her and her boyfriend together. While I didn’t unfriend her, I did “unfollow” her. True to a habit I’ve been guilty of for years, I didn’t want to completely sever the connection, but I didn’t want to look at her relationship either.

The Tiger Ticket Pivot

Fast forward to the spring of 2025. Sierra sent me a Facebook message about Detroit Tigers tickets. Anyone who reads this blog or follows my social feeds knows I bleed Tigers baseball. She had some unused tickets available through her work. The organization has a policy that if a certain percentage of tickets don’t get used, the business doesn’t get offered them in the future. So, she messaged and offered me some free of charge, asking how many I wanted. I appreciated her generosity, but didn’t want to go overboard, so I said four. All in all, I went to four or five games last season with tickets I got from her.

I was polite, I thanked her sincerely on multiple occasions, but I always felt like I needed to do something to return the favor.

Fast forward a few more months. I started looking at her social feeds again, and there were no longer any photos of her and her boyfriend. It was as if she had scrubbed both timelines. I definitely took notice, but at that point, I was seeing Veronica. Things were still going okay there, so while Sierra was on my radar, I wasn’t acting on it. Shortly after that, things with Veronica completely fizzled out.

Eventually, Sierra and I started chatting online again, bonding over some political posts and striking up a conversation. Finally, when I worked up the nerve, I messaged her: “I really appreciate you getting me those Tigers tickets last season. I’d really like to do something to return the favor. Would you like to get a drink sometime? My treat. Absolutely no pressure.”

She agreed. To be completely honest, I definitely had a bit of an ulterior motive. I had never met her face-to-face, and I still wasn’t entirely sure we’d ever even heard each other’s voices. But she was the lingering “what if” in the back of my mind. To channel my inner Clint Eastwood: I gots to know. Even if nothing came of it, I needed to get to a point where I could stop asking myself what if.

We met at a bar about 10 minutes from my house because she happened to be on that side of town for a graduation party. We hung out, had a few drinks, laughed, and talked for about two hours. I remember her saying as we were leaving, “We should do this again sometime.”

We texted a bit more after that, and finally, I asked her out on an actual, official date.

The rest, as they say, is history in the making. It’s been just over two months since that first “thank you drink” meetup. Things have just gotten better and better. Just this past Thursday night, right before she left town, we both dropped the L-word on each other.

Closing the Doors for Good

The irony and serendipity of it all isn’t lost on me. Seven years ago, we just missed each other. But I also know that seven years ago, I wasn’t the person I am today; I was still operating under the false assumption that I needed to be with someone to be happy. Time on my own taught me that isn’t true at all.

More than that, for a long time, I was terrified of throwing anything or anyone away. There’s a moment near the end of The Breakfast Club where John and Claire look inside each other’s wallets and purses. Claire can’t believe John keeps photos of so many girls, and says, “I guess I don’t want to throw anything out.” John replies, “Neither do I.”

I was like that for years, keeping old exes and “maybes” in my back pocket as social media safety nets—not because I cared enough about them to close doors, but because I was afraid to throw anything away.

Being with Sierra changed all of that. I’ve removed my foot from all those other proverbial doors. I’ve closed off ties with those old ghosts and backup plans. I’m 100% dedicated and committed to Sierra, proceeding with sincere intention. She sees me exactly as I am, warts and scars and all.

Every relationship eventually faces its real tests—the friction, the hard days, and the outside noise trying to creep in. We haven’t had to weather a heavy storm yet, and I know learning how to handle those moments together is part of the journey too.

I don’t need a backup plan anymore. Right now, things are looking very, very good. And for the first time in a very long time, that is more than enough

Rebuilding a life takes grit, consistency, and a lot of ‘Option C’ thinking. Having crossed the 1,000-day milestone, I’m now charting the territory beyond. The mission remains the same: No glitz. Just the work. New to the blog? Start your journey here to see the blueprint and the ‘Tricorder’ perspective behind the rebuild.

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The article “It just took me 7 years to ask her out”

Rebuilding Rob