The One That Got Away


Dear Dharma,

Everyone has a relationship story about the one that got away and this is exactly what I feel has happened to me.

Back in my early twenties I broke off a fairly serious relationship because I wanted more freedom to live life and thought it was too early of an age to be attached to one person.

Now, later in life I realize that this may have been a huge mistake.  I have had other relationships since then but am single now.  I often find that my thoughts come back to this person after all these years and then I start going through the long list of what if’s. Then I feel remorse, like I’ve let myself miss out on something. This has to mean something, doesn’t it?

Now for the real question, what do I do about it? Do I make an effort to reconnect or do I just leave it alone and let bygones be bygones?

Wish I Had a Time Machine!

Dear Time Machine,

I have a saying that I try to live by – that I’d rather regret what I did, rather than what I didn’t do.  Of course, I try not to apply that theory blindly, but the concept as a whole works for me.

So in saying that, I am basically saying go for it.  Except not blindly… you need to first confirm that this person is single and interested.  Other than that criteria, why would you not?

To break off a relationship because you had enough self-awareness to know you felt too young to commit for the long haul is admirable and honest.  A lot less drama would exist if that happened more often, IMHO…  To try and re-open this door is A-OK with me, as long as there’s interest on both sides in doing so.

Next Steps

I can’t tell by your letter what type of access you have to this person, but I’m assuming social media is going to play a role and I’m assuming you are going to send a message of some kind. Keep it light…  “Well hello there Pat! I was recently looking back at some photos from the good old days and I was wondering how you are doing and where life has taken you! Would love to hear back from you…”

And actually, if for whatever reason you were not able to determine marital status prior to this, any response you get should clear that up.  If you get a “Nice to hear from you! I’m recently married with twins!”, you’ll know to drop it, right?

But if easy conversation occurs, go with it.  If it leads to a phone conversation, great!  If it leads to coffee, fantastic! Somewhere along the way, you’ll know if this is a go or not… And if not, well, at least you’ll know you tried, and there will be no regrets to live with.

Even if you get no response at all to your initial message, that’s how you’ll need to look at it.  Not everything we think was meant to be has a fairy tale ending, I can assure you.

Would love to hear back from you on this, to know how things go!  My fingers are crossed for you…



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