Pete –

First of all, you are not undeserving of anyone. Those thoughts you have, that tell you that someone is better than you are, that they are out of your league, that you will never be able to be with them, they are doubt. Doubt should be arrested for murder, because it has killed more dreams than failure ever has. My wife was severely out of my league. But I was young, and I had some serious swagger, and probably a little too healthy opinion of myself. A whole lot of women are attracted to men with a good amount of self esteem. Because if we think that highly of ourselves, then we must think quite highly of them seeing as we want to be around them. I was terrified, like you, and thought “I am gonna tell this amazing, charming, beautiful woman that I think all of those things about her, and she is gonna laugh in my face and tell me to get lost”. We have been married for almost 15 years and have 4 kids.

But what happens if she does? Is the sun no longer going to rise and set? Are the tides still going to come in and out? Your worst case scenario is that you have an awkward interaction with her and then apologize after saying how she made you feel, but that you just had to take the chance because you would have regretted it always if you had not. Do not act aloof. Nor repentant. Act as though you took a chance, you failed, you would like to move on as friends, and then do so. Do not be awkward around her. If she asks if you will be, pull a Jim Halpert and say “Oh. yeah. Totally awkward. I hope that’s okay” and have a laugh with her. If she gives you the “I would rather just stay friends”, then at least you know, and will never second guess yourself. If that is amenable to you, say you would love that and are glad to have her as a friend. If that is something you can’t get over then you move on. That last part….hardly ever happens. But here is the thing. That last part hardly ever happens because we men think that if we just persevere, she’ll see us as a viable candidate some day. Maybe. More than likely not, however.

But your best case scenario is that she says she also feels that way about you, or at the very least is interested in seeing if she also would like to see you. Do not attempt to talk down the other guy in order to make yourself seem more compatible. Just tell her how you feel. Exactly what you told us here…..she makes you smile. Even when you don’t feel like it.

Your one decision must be is it worth it to say something. I have never once heard of someone in your position making their feeling known and then even the friendship imploding outside of the man with hurt feelings being unable to get over the rejection. If you  can handle that possibility, then you have nothing to lose. If you can handle that she might tell you she just wants to be friends (or in severely, unheard of in my case, rare occasions where they break off all contact), then you literally lose nothing. Your worst case scenario is you end up where you are …..right now.

A study was done of palliative care nurses (end life/nursing home) asking the people they took care of what their biggest regret was as they neared the end of their lives. One of the biggest regrets was not telling someone they cared about how they felt. This is one regret you can avoid now, and all it might cost you is a little bit of your ego. Considering what you might gain in the bargain, totally worth it.

Keep your chin up. Believe in yourself. Don’t let the world grind you down and feel bad about you. You are deserving of love and happiness, and you will find it, one way or another.