[TooMuch]

This is a long story, I’ll try to be as brief as possible.

I’ve known this woman almost my entire life, We went to high school together and are now in our late 30’s. Once, while still in school, we almost had a chance to “test the water” with a relationship, however, at the time, there was drama with other friends, and we decided that respecting other’s feelings, and sacrificing this chance was better for everyone involved. This was my first mistake, instead of holding to my values and letting her know how I really felt about her, I allowed her to convince me that it wasn’t worth the risk.

Years after that, we went our separate ways, and kept in touch irregularly. She has always been in a relationship with someone, I think partially out of a internal fear of being alone. Because of this, I never tried to get in the way of any of the other relationships she was in, not wanting to put her in a position to have to choose between two men. Sure, there was a aspect of fear involved in this for me, of being rejected etc, which is where my second mistake comes in. I know I should have been more assertive and allowed her to make her choice instead of take that choice away from her and make it myself.

As the years go by, I move out of state, and we still kept in touch, which escalates into deeper and more meaningful conversations, all over again, I feel our relationship moving towards a greater bond and something more. I know she’s dating someone at the time, but I try to learn from my mistakes and feel that it’s only right for her to know the truth. I decided to move back to my hometown, where she was too, so that I could be there when I told her, instead of trying to explain things all over the phone.

A week or two before I finally moved back home, he asked her to marry him. She said yes. I never did have a chance to renew with her and explain the feelings I had. This time it took on a more devastating blow. I’ve always feel such a strong bond with her, and in some aspects I think she feels the same way. However, I could never get the balls or the timing right to breach the subject any further.

After the wedding, she moved out of state and we lost touch (my doing) for quite some time. I’m thinking it’s been at least 8 years. I didn’t want to get in the way of her happiness, and didn’t feel like I was strong enough inside to not become resentful to her for the mistakes that I made. I felt that letting her go was the right thing to do.

Since then, I’ve done very little dating, and always seem to hold her as the bar that my other failed dates/relationships were being measured to (As few and as far between as those have been). I know this isn’t right, and some might say that I should just let go, but my heart, faith, and reasoning tell me that I have to be true to myself.

Last night, she was in town and wanted to reconnect. I almost avoided the situation, feeling nervous and uncomfortable, but she’s always been an amazing friend through the years, and despite of the mistakes I’ve made in the past, and the secret that I’ve spent my life hiding from her, that she shouldn’t be the one to suffer because of it. I accepted the invite, and went to her folks house to celebrate her mothers retirement. (I’ve always been a very close friend of the their family)

As you would expect at this point, I couldn’t believe when I saw her again, my heart skipped beats over and over again. She’s even more beautiful then she’s ever been, and I thought that I had such strong feelings for her because of who she was back then, but after talking for over 5 hours, I was amazed and completely blown away at the woman she has become. Not only did it reinforce everything that I’ve had buried inside all these years, but added that much more too it.

I found out that she’s been divorced now for a little while, (less than a year I think) and has actually started dating again as well. I’m also not the man I was before. I know that she has a right to know how I feel. regardless of the outcome, and I know that it’s the best thing for me too, to give me closure on something that I’ve held back for years. I need her forgiveness for being selfish and loosing touch with her all those years ago. It’s the right thing to do.

However, I’m concerned with dropping a thermonuclear bomb like this and the “WTF” factor that could sure be impending after just reconnecting after a few days.

I’m very interested in hearing your thoughts.

Thanks for your time,

TooMuchHeart?

[April Masini, your AskApril]

You’re making way too big a deal over this. You missed decades of opportunities and have lived with regret. Now, you’ve been given a second chance. Ask her out on a real date and don’t turn this into something thermonuclear. Just have a good time and get to know her as a date — not a friend. 😉

[Member]

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