Q. I cheated on my ex. I'm extremely ashamed of this part of my past.
I understand now why I did it: to avoid facing a painful reality, and to avoid sharing my feelings with my ex because I was afraid of his reaction. I've grown immensely since then.
I am dating again now. I am afraid of sharing the details about my past with prospective partners because they'll think, "Once a cheater, always a cheater" -- which, granted, is what I thought before I found myself in that boat.
At what point in a new relationship do I open up about this? If it's a deal-breaker for someone, they should know as early as possible so they can make an informed decision about being with me, but I also want to feel that they know enough about me to understand me and possibly grant some compassion for the confused, hurting girl I once was.
A. You bring it up when it comes up, be it the first date or the 40th, as you would any other aspect of your past -- that you and an ex used to love old movies, that you were in the AV Club in high school, that your mom used to scream at you for spilling things but was the soul of patience when you crumpled her car.
Do I minimize cheating by suggesting this? Perhaps, but that's not my intent. I'm merely arguing that your infidelity was not some isolated, atypical appendage to the rest of your life that has to be offered up and explained. It was, and is, a point on your progression through life. A significant and bad one, sure, one you'd be wrong to go out of your way to conceal. But a date would be just as wrong to judge you solely on this incident.
That's because your cheating had context that warrants just as much concern and attention from a prospective partner as this single outcome.
Your cheating was about painful-truth avoidance, right? So your immaturity is that meaningful context -- including its source and manifestations (surely cheating wasn't the only one), and your progress so far in overcoming it. The "details about my past" are the trees; potential partners owe each other the forest.
Conveniently, that's also what you owe yourself -- with the cheating and whatever else you have done and will do wrong, as well as the good things you bring to this earth. View yourself as a flawed, complicated and evolving whole, one who doesn't lie to herself or others about her limitations, or exaggerate her gifts -- and who deserves someone who will embrace her as such.
Once you're comfortable with yourself in this way, the question of what, when and how to tell will all but take care of itself.
Q. I'm getting ready to graduate college, finally. I took the nontraditional route due to parental meddling. I find that I'm likely not graduating cum laude, something I was really looking forward to.
I know it's just a title, and means nothing in the real world. But I can't help but feel I let myself down. I'll graduate with two degrees and a diploma from my school's honors program, but it doesn't feel like enough. This was the time to prove myself, and I don't know if I did.
A. I could argue this is the time to prove yourself, as you start a phase of your life without the tidy, black-and-white goal of academic honors to guide you. While college coursework is rarely easy, slaying the "parental meddling" dragon was at least straightforward: Get a college degree.
Done. Well done, actually -- congratulations.
Now, with that behind you, I suppose you could look again to your childhood to find another dragon to slay, but that'll just put you in this very spot a few years down the road.
Instead, I suggest you elevate your sights to finding, living and appreciating the life that suits you best -- not just one that proves a point.
Q. Last year, my brother and I each inherited a significant amount of money. His entire share is already gone, mostly to pay off home renovations. Now, he and his wife are talking about another major addition. This is after they've sunk at least $300,000 into a house that has dropped in value by about 10 percent since they bought it.
I know it is their money (or was), but it kills me to see my grandparents' lifetime of hard work vanishing. How can I talk them out of this, or, if that isn't possible, how hard can I bite my tongue before it comes off?
A. A tongue's bite tolerance is for a different columnist, but boundaries, I'll do: How can I explain to you that this is so far outside the scope of your business that it defies comprehension?
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