DW 1/20

My boyfriend’s younger years were wild, and he has a pretty extensive criminal record to show for it, including prison time. Although some of the consequences of his past irresponsibility will follow him forever (e.g., limited career opportunities), he’s been an honorable, hardworking, and law-abiding citizen for as long as I’ve known him. My mom and sister, who I talk to all the time, were very skeptical when I first told them about his past, but after months of hearing about our relationship and his character, and meeting him a few times, they seem to respect and genuinely like him. But they both warned me from the beginning not to tell my conservative dad and stepmom about the skeletons in his closet.

It’s been two years now, he and I live together, and I still haven’t told my dad and stepmom about his past. They seem to have a favorable impression of him so far, but they live far away and have only met him once during these two years. I feel guilty about keeping such a big secret from them for so long, it’s awkward having to tiptoe around their questions about his history, and it’s hard to do so without lying or looking like I don’t know anything about the person I share my life with. I want to tell them and just deal with however they react, but my mom and sister still insist that they never need to know because it’s in the past and it will only become less important as time goes on. What do you think?

A couple of years ago I was dating my loser of an ex boyfriend and on our way to a concert in Tennessee, we got pulled over. He had marijuana in the car and I knew this, however it was his – not mine. He had a previous felony for marijuana and asked me if I would take the blame for it. The police officer that pulled us over said that one of us had to take the blame for it and that I would be the better choice because I had never gotten in trouble prior to this incident. The officer told me that I would have to fly back for court, pay some fines, and after a year of probation, it would be cleared from my record. My ex promised to pay for it all and talked me into taking the blame. I know, I know, stupid mistake… I’ve rethought this situation a million times in my head and would change it if I could but unfortunately that is not going to happen.

Flash forward to present day and I have parted ways from my awful ex who didn’t pay for anything or do anything he said he would do. I am, however, dating this awesome guy and I am really into him. We have only been dating for about a month and my past hasn’t come up in conversation. We live close to the Canadian border and he keeps bugging me to get my passport and go to Canada, and I keep saying I will but really I’m just procrastinating. Canada is super strict on crossing the border and will not allow anyone with a misdemeanor or felony that has occurred in the the last 10 years enter. I know I have to tell him soon because I can’t procrastinate forever, but how do I tell him this?

~ Living with Regret