This 48-year-old man and his ex-wife, who is 47, had been married for seven years before they got divorced about 15 years ago.

At the time, the reason for their split was simply that they had different visions for their future. He always wanted a family and imagined living the “white picket fence” life. His ex-wife, on the other hand, valued traveling and didn’t want to be tied down.

Still, while there are clichés about remaining friends after divorce, he and his ex were able to remain friendly– at least in the beginning.

Even after his ex met another older and wealthier man who was able to provide her with the lifestyle she wanted, they stayed connected.

And when her ex got married to the other guy in 2010, he was actually invited to the wedding and even delivered a short toast.

“Obviously, with the guy in her life, we drifted apart, and we basically played Facebook tag,” he said.

After they got divorced, though, his mental health state was not that great. He was initially depressed and went to therapy following their split.

Then, once he watched his ex get remarried and start “gallivanting” throughout the Caribbean and Europe, he became even more depressed.

Therapy also helped, but it was not the complete solution. So, it really took him a whole five years to pull himself out of the slump and become “himself” again.

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At that point, he decided to try dating again, too, but none of his efforts ever really worked out.

“I honestly felt that I could have never been happier with anyone than I was with her. I regretted putting my foot down about how I wanted to live,” he revealed.

Yet, while he was struggling with the end of his marriage and trying to get back into the dating pool, his ex-wife was posting on Facebook– documenting her attempts at becoming pregnant.

This was beyond shocking for him since it was the one thing she was completely against in their own marriage. In fact, she even wanted to get her tubes tied at one point “just in case” of anything.

Regardless, with her new Husband, his ex-wife tried everything, including fertilization clinics and IVF, but nothing worked. Eventually, she announced that a surrogate was carrying her child, but the baby was tragically stillborn.

As if things couldn’t get even worse, his ex-wife’s new husband also passed away in 2021. Everyone only found out about a month later since the burial was very private.

Once he heard the sad news, he decided to reach out to his ex-wife with his condolences.

“I messaged her saying I would be there for her if she needed someone to talk to,” he recalled.

“I did not hear back. Aside from posting inspirational messages, etc., she went dark.”

On his birthday this year, however, he did receive a card from his ex-wife. She wished him well, thanked him for being a really important part of her life, and also claimed that they might be in touch soon.

Well, this past Friday, his ex-wife followed through on her last statement. She gave him a call, and it was the first time they had directly spoken in over 10 years.

They both kept the conversation light, and he didn’t really bring up anything that had happened over the last decade. Regardless, his ex asked if he was free to grab a drink or coffee on Tuesday since she was coming to town.

He agreed to meet up, too, and since then, they have begun texting back and forth. According to him, some of their messages have been a bit more intimate.

“I get the sense she’s testing the waters, so to speak, to see if there is interest there,” he detailed.

“From my end, this is a double-edged sword. There really would be interest in seeing where it might go, but I don’t think I could handle losing her a second time.”

He has since confided in a few friends about the situation, hoping to get their perspectives on potentially meeting up with his ex. But his social circle has been pretty torn. Some friends believe he shouldn’t get involved; meanwhile, others think that he should just see what happens.

So now, he’s been left feeling pretty confused. He isn’t sure how to navigate rekindling a relationship after so long, and he doesn’t know what red flags to be looking out for.

Have you ever been in a similar situation? Do you think he might regret not exploring the possibility? At the same time, if it doesn’t work out, is it worth suffering such heartbreak again? What would you do if you were in his shoes? 

You can read the original post on Reddit here.

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