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April 24, 2007 / missknowitall

It’s Not Too Late To Reclaim Lost Love

Dear Little Miss,

I am 23, living on my own and, for the most part, happy.  I date and I hang out with friends a lot.  One regret that I have always had is letting my high school sweetheart get away from me.  When we graduated I broke up with him because I thought we should experience life.  I regretted that decision the day after it was final, but I thought I was just being a needy baby.  I have tried to be strong and to forget him, but I haven’t been able to.  I compare all men to him and none of them measure up.  I have been keeping tabs on him all these years so I know that he has been in a serious relationship for the past 3 years.  Well, just the other day I bumped into him at store!  I wanted to just die, then and there.  He asked if we could meet for coffee this weekend to “talk about old times”.  Now I am agonizing over whether I should tell him how I feel when I see him again, or if I should just leave him alone so I don’t upset his current relationship.  What do you think I should do?


Dear Regretting Lost Love,

If this guy were married I would definitely tell you to just leave him alone.  But, the fact that he isn’t married shows that he is leaving his options open in life and I see nothing wrong with you presenting yourself as one of those options.  So, lets take a look at this from all angles.  If you don’t tell him then you choose to go through life with regret, longing, and the inability to fully love any other man.  If you tell him and he says “Sorry, Toots, I’ve got a gal” then you can hate him, get over him, and get on with your life.  If you tell him and he says, “Wow, I wish I had known you felt this way.  But…” then at least you know that he knows, and you never know, he might come back to you in the near future.  If you tell him and he says, “I’ve always felt the same for you” then you have an awesome chance at some Hollywood style romance (Just make sure that he breaks up with his girlfriend first.  Do NOT be a side dish entertainment while he carries on a public relationship with the other woman).  So far, all the good outcomes come from telling him.  Now, lets talk a bit about how to tell him.  I suggest you write out your feelings for him in a letter.  This will help you get your thoughts all evened out.  Take the letter with you and if you find you are too embarrassed to tell him, or if he has brought his girlfriend along and you can’t tell him, then just hand him the letter as you part.  Make sure you give him your contact information in the letter.  Afterwords do not sit around pining.  Keep going with your life.  If he ever does return to you, you don’t want him to find you an emotional wreck or as a needy, sappy, Ben & Jerry’s kind of mess.  You want him to find you confident, happy, and leading a fulfilled life so that he will want to share in your awesome life with you.  

I leave you with a quote from Sydney Smith:  “Regret for the things we did can be tempered by time; it is regret for the things we did not do that is inconsolable.”

Unregrettably yours,

Miss Knowitall


One Comment

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  1. waited too long / Sep 28 2007 9:08 am

    Dear Regretting Lost Love,

    If he is not married, you MUST tell him how you feel or you will end up in my situation. I broke up with my HS boyfriend 20 years ago for similar reasons. I have never gotten over him. I heard from him recently, after two decades of silence, and in the course of our conversation, we both said that we have always wondered “what if” and that if we saw each other now, we would have a hard time letting go. But now it’s too late…we are both married (to other people) and have kids. It’s no longer as simple as your situation. He and I both realize that to continue that conversation would be the wrong thing to do, so we are not going to put our families at risk by carrying out an emotional affair. But I am heartbroken. I hope that I can save you from this pain… GO TALK TO HIM and tell him how you feel, NOW, before it’s too late.

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