Red Responds: A Grown Woman Pining for Her High School Sweetheart

Dear Red,

My class reunion is coming up, so I went on one of those reunion websites and located my first love. Now to be honest, I have searched for him off and on for roughly five years now. He was such a wonderful guy…and I hurt him pretty badly.

Well, I found him, and we have conversed briefly via email. His emails and his phone calls come across as very guarded, with a splash of hopefulness towards us reconnecting in a romantic sense. My concern is that I have been communicating with him more than he has with me. Each communication he sends is like a carrot dangling in front of a rabbit…I respond quickly, and he doesn’t respond for a week or two.

Now, as I mentioned before, I hurt him pretty bad, and he has even made reference to it in previous communications. I have really opened up to him about my life of the past 20 years, but he has offered up little information to me about what he is up to these days. However, I find if I don’t respond to him in a couple of days, BAM! An email appears. As I write this to you it sounds pretty foolish to me — a grown woman pining for her high school sweetheart.

I guess I just need validation that I am barking up the wrong tree here. I’m really feeling there is a connection between us…our communications have been very thoughtful and sweet, not erotic or suggestive. Just chats between two people who experienced first love with each other. He says he doesn’t want to lose me again, then takes weeks to respond to a simple email, claiming he is ultra busy at work. I travel for a living, and always seem to be able to find the time to drop an email to him while I’m on the road.

I am ready to throw in the towel, and was looking for any suggestions you might have for me. I’m 38, established, and feel kinda stupid that I seem to keep doing penance for the pain I caused someone I haven’t seen in 20 years, but feel I love very deeply still.

Thanks for any words of wisdom you can give me.


Dear Susan,

Let me just start out with a flashing “proceed with caution” sign for you, because that’s what he’s doing.

Your sweetie does tend to get tied up with work, as well as the rest of his life.

While he does think of you, and does toy with the idea of reconnecting with you, he is and will continue to be very cautious. Allow him to have that for the time being. He is facing many decisions regarding his future, and you seem to have come in to lighten as well as complicate the situation for him.

There is female energy around him at the current time. I’m not sure if it’s an ex or a future ex, but she’s there even though things aren’t what I’d call a happy relationship situation. Don’t pressure him about this. He’ll tell you all there is to know when he is ready.

I don’t see the two of you coming together fast and furious for a passionate romance, but that doesn’t mean that I’m not seeing the passionate romance. It is a timing thing with the two of you. Now doesn’t seem like the “right” time; but if you continue to keep in touch, that can drastically change in late winter or early spring.

The best way for you to proceed is slowly. There is a connection between the two of you, but it is one that needs to be nurtured. Before you throw in the towel, why don’t you sit back and enjoy what is being offered? At the very least, it is friendship. The potential for more is there as well.

Your feelings for him are based on the history between the two of you, and that isn’t going to go away over night. So while I can in no way tell you to base your future around this guy, I can tell you that your life has been a little brighter since he’s come back into it. Why give that up? Give this man some time to figure out what he wants, and allow him to take the lead.

While things may not be progressing as you would like, they are progressing. This time around, things can not be forced or rushed. While I am definitely not suggesting that you put your life on hold until he figures his out, I am suggesting that you not close the door in his face. If you do, it will be for the last time.

Brightest Blessings,
Ext. 9226

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