What It Looks Like to Find Love After Heartbreak

This man finally found love after heartbreak. Read his story.

Family gatherings come with all kinds of precious small talk, and all my fellow single people out there know that these events raise an inevitable question: “So, Isaac, you dating anybody?” It’s become something of a family tradition.

For me, it’s not quite enough to put a damper on these get-togethers because I’m fortunate to have an amazing family and therefore some amazing family gatherings. But I would be lying if I denied ever thinking to myself during the holiday season, “Oh, another Christmas without a significant other.” It’s almost as if there’s a running tally being carved into the wall of the lonely confines of singleness every year that I fail to find that *special someone* and bring her around to meet the family on Christmas Eve. Not to be overly dramatic or anything.

In all seriousness, there certainly are moments when I wonder if I’ll ever find what I’m looking for — even when I’m living my best bachelor life. And when I don’t feel like I’m top of my game, I’m especially tempted to lose hope. During these moments it’s especially helpful for me to remember the heroic men who have boldly gone before me — whose fates seemed perhaps even more hopeless than mine! — and to recall how they found love even after incredible heartbreak.

One of those heroes is my friend, Paul. I had a front-row seat to his heartbreak, but he persevered and eventually found the love of his life. Here’s his story.

The dreaded “friend zone”

Paul and I go way back. We lived with each other a couple different times and I was privy to his long struggle of being “always the friend but never the boyfriend.” So I was pleasantly surprised to hear that he had met a girl at a bar in Rome, of all places, and got her phone number and took her out on a date or two or three. Then I was not so surprised to find out that he had somehow, somewhere slipped into the dreaded *friend zone*.

But while Paul was certainly dismayed by this development, he was not defeated. Freda was a rather charismatic woman who was as attractive because of her magnetic personality as much as her soft-yet-striking features. Add in an irresistible foreign accent, and you can see why his feelings for her lingered. He continued to spend time with her, proved his worth to her, and they began a romantic relationship.

This continued throughout the rest of his time overseas, and I took particular pleasure in seeing him so energized — truly happy — in his relationship. And it was clear that he took great satisfaction from that fact that he had won her over. She took some convincing, and yet he was up to the challenge.

A broken heart

As he was set to depart her company and return to the U.S., she expressed some skepticism that their relationship would be able to withstand being thousands of miles apart, but Paul was adamant they could make it work. Freda was willing to give it a chance, and they kept it going for a while, even after he left. Things seemed to be going well enough, and she even offered to pay for half of a plane ticket for him to visit her in the U.K.

Then, without much warning, her feelings changed. She decided she didn’t want to date anymore, but they could remain friends, and she would be happy to still host him on his visit. When Paul told me and our other roommate that this happened, we were crushed for him and expressed our shared sorrow. But then we were confused. “Wait, you’re not going to still visit her… are you?” we asked, incredulously. “I’m going to go win her back,” he said, confidently.

Well, he did visit her, and no, he did not win her back. I’ll never forget the Skype conversation we had when he was sitting in her apartment and explaining to me how she wasn’t being persuaded by his continued overtures. But not only that — she had the gall to flirt with another guy right in front of him. He broke down in tears — sobs, actually — as he explained how disappointing it was and how embarrassed he felt to have flown halfway across the world to be rejected by this woman. My heart broke for him.

Another fish in the sea

But, of course, that wasn’t the end of his story. Paul took the hint from Freda this time and realized he was going to have to be another fish in the sea.

It turns out he didn’t have to wait long. That following Christmas, Paul ran into Lou at a birthday party. Lou was living a state over, but visiting family for the holidays. He had already admired Lou for a while — from afar. Looking back, there’s no doubt in my mind that God, in His providence, had intended for them to meet again at that birthday party. But at the time, of course, there were no guarantees. Paul knew he had a limited window of opportunity, so he decided to go for it and invite her to a New Year’s Eve party we were going to host at our place.

There was just one issue: we weren’t planning a New Year’s Eve party.

No matter. We threw the best damn NYE party of all time, and Lou came, and they hit it off again. They continued to talk but weren’t yet to the point of having any sort of define-the-relationship conversation before she went home after the holidays.

Paul was undeterred — he called up a buddy of ours who’s a priest who just happens to live near-ish to Lou, and asked if he can come visit for a “retreat.” He then told Lou that he was going to be in the “area” and asked if he could visit her. She obliged, they had a nice weekend together, and they started dating. Ten months later, he proposed marriage and now they’re on their way to happily ever after with a bouncing baby boy.

Clinging to hope

I think back from time to time on Paul and his rock-bottom moment in that Skype conversation. I’m sure he was tempted to despair then and in the weeks and months thereafter. And it would have been easy for him — understandable, even — to wallow in self-pity and allow it to keep him from pursuing his goals of a loving relationship.

Instead, he put himself right out there and on more than one occasion went out on a limb to pursue Lou, without any guarantee that he wouldn’t fall right back on his face again.

That’s the funny thing about pursuing the vocation to marriage, isn’t it? We know that God wants what’s best for us and is pleased to provide it. But that doesn’t mean there won’t be bumps in the road — in fact, there typically are, from my experience. Romantic relationships are rarely (if ever!) clear and obvious, even up until “I do.”

Part of our role in this particular vocational journey is to navigate the bumps, twist, and turns, which may include a U-turn or even a crash here or there. Our task is to put forth the necessary effort on our end of the bargain, trust along the way, and remain faithful to the end.

For me, then, I don’t worry whether it will all work out in the end, but I do struggle with losing hope in the meantime. I’m worried I’ll end up settling, that I’ll grow impatient and cut corners, perhaps seeking fleeting consolation in the meantime instead of trusting the process.

Paul didn’t do that. And it’s provided inspiration for me to do the same — to not lose hope, even when the circumstances seem bleak, even when there’s not necessarily change in clear sight.

And in the meantime, I’ll continue to hone my party-planning (and throwing) skills — because you never know when you’ll need to throw one in a pinch.

Grotto quote graphic about love after heartbreak: "We know that God wants what's best for us and is pleased to provide it. But that doesn't mean there won't be bumps in the road."

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