Wow, the things I would change if I could. But actually, in hindsight, I wouldn’t change a thing. Your mistakes make up who you are and the possibility of who you can become, much better than your success. So don’t be so hard on yourself!
As for practical advice: Ask her out! Don’t be afraid she’ll say no. At the end of the day, you barely remember the no’s. You get over the embarrassment, but the never asking — you never forget those. And when she says yes, just be yourself. You’ve way more to offer than you give yourself credit for. And speaking of credit, when you pay with your credit card, on your first date, DO NOT write on the back treating your date like a tax write off. She did not like that!
Follow your gut. It always steers you due North. Be good and true, kind and honest. In the end, it’s the acts of kindness people remember.
Be out. Don’t be afraid. And I’m proud of you that you told everyone in your family that you are gay. BUT you never actually told your Father. And even though he never mentions you are gay, he’s always telling you he read about you so talk openly. The room is not big enough for that elephant, too. And assure yourself, no matter how he responds, he’s proud of you. Don’t let your fears get n the way of allowing him to accept you, just the way you are. And even if he doesn’t, speaking your truth is far better than living in a shadow of who you really are. Live out loud, and bold. Always.
And never ever hesitate to go out on that limb. It’s where the fruit is.
Do more of what feels good and less of what doesn’t. Seriously, That one’s a big one.
And lastly, through all the trials and tribulations of your career and personal life, take the high road, always, no matter how tempted you are, or wronged you feel. The one thing about the high road many people never even get to experience, ’cause they didn’t take it, is how sublime the view.