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 since he had a previous felony for marijuana, he asked if I would take the blame for it. The officer that pulled us over 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 everything, so I took the blame, a decision I wished a million times I could go back and change.
Flash forward to present day and I have parted ways from my awful ex who didn’t pay for anything. I am, however, dating this awesome guy I’m really into. We’ve 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 so we can go, but 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 to 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
First things first: you need to make sure you really aren’t allowed across the Canadian border. I’m certainly no expert, but even doing a a few minutes of Google sluething, I found information that suggests you may actually be allowed into the country after all. You should contact the Canadian visa offices and explain your situation and find out if you are “eligible for rehabilitation at a port of entry,” and what documents you would need to present at the border. Next, don’t be so hard on yourself. Your biggest mistakes were being naive and overly trusting (and, OK, maybe a little not-so-smart). Hopefully, you’ve learned from those mistakes and you’ll be more discerning about whom to trust, and you’ll never, ever again take the blame for someone else’s criminal offense.
As for how to tell your new boyfriend about your record, you can say exactly what you’ve said here. In fact, you can just show him this column if you want (hopefully, you’ll get some words of support in the comment section to boost your courage). Explain to him that you made a mistake you greatly regret that unfortunately has long-lasting effects, which may or may not include being turned away at the Canadian border. And then you can suggest taking a longer road trip instead. Mexico is very nice this time of year.
Last July on vacation I ran into a husband of one of my patients who had passed away the December before. We were each there with children and friends, and our groups sat together on the beach every day. He even came down to my beach house one night and spent the evening relaxing on the porch with me and my boys. There was chemistry, but I wasn’t quite sure if he was ready for a relationship after losing his wife just several months prior. At the end of the week we said our farewells and he said he may stop by my office to stop and say “hello” sometime. I didn’t hear from or see him after that until this December (the week before Christmas). He came into my office, we chatted, hugged. He asked if I was seeing anyone, and if I’d like to go out sometime. I replied “yes, I’d love to.” We then exchanged phone numbers and agreed that we would get together after the holidays. He began to leave, and again we hugged, he kissed me on the cheek, and then he held both my hands and told me how beautiful I was and how he looked forward to getting together.
Later that day I texted him saying I was glad he came in and I looked forward to seeing him again. He texted back that he was too. Then that evening I again texted him saying, “Thank you for the smile you have put on my face all day.” No response. The next day, my plans for that evening fell through so I called him to see if he might want to go out that night. He said he was busy with his son and some friends, but that depending on how late he got in that night, maybe breakfast the next day would work. He said he’d call if he was able to meet. I did not hear anything from him the next day. So Christmas came, and I sent out texts to my friends group, which included him, saying Merry Christmas. Again, no response. I decided not to contact him again, but to leave it in his court. However, after thinking and discussing it with a girlfriend I began to worry maybe he hadn’t gotten any of the text messages and that was why he hadn’t responded. So about two weeks after Christmas I called and left him a message — the “how was you holidays, would love to get together, call me.” Still have not heard anything from him.
Was I too forward or too persistent? In the past I have been told that I can have a “cold shoulder,” so I thought I would try and be a little bolder. Now I am scared it backfired. Or could he still be just be processing his wife’s death since she died just a year ago? Now I have exhausted every avenue — text, phone — and I am totally baffled why I have not heard back from him. Please help!! — Totally Baffled!
It would seem, Totally Baffled, that a recently widowed man whose dead wife was a patient of yours probably wasn’t the best choice to test out your new “going bold” tactic, especially if the time you chose to break it out was his first holiday season without her. Absolutely, he’s still processing his wife’s death and likely will be for quite a awhile. That doesn’t mean he won’t be ready to date eventually or even that he isn’t ready to date now. But, just because a widow is ready to dip his toes pack into the dating pool, doesn’t mean he’s ready to dive in headfirst. The mistake you made wasn’t in pursuing this man, but in pushing him into the deep end before he was ready.
Generally, if you want to avoid being overly aggressive, a good rule of thumb to remember is to not text, call or email someone more than two times in a row without a response. If the other person happens to be a recently widowed man whom you have a planned date with after the holidays, it’s best to tread even more lightly and simply wait until, you know, after the holidays to get in touch. Imagine how sad he must have been feeling during that period — how much he was probably thinking about and missing his wife. And then he gets multiple messages from another woman he hasn’t so much as been on a single date with yet — a woman who was actually his dead wife’s health care provider — and instead of wishing him well during his first holiday season without her, the messages are almost predatory in nature. He probably felt pressured and a little guilty, which is why you didn’t get a response.
I’m sure it wasn’t your intention to push too hard too fast or to be insensitive to what were surely mixed and complicated emotions on his part, but you did and you were. Your best bet now is to back off. If there’s even the smallest chance the widower is still interested in going out with you, you’re going to blow that chance to smithereens if you reach out before he’s ready. Lay low, play it cool and take the lesson to be learned here: patience is a virtue. And if you happen to run into the widower again some time — around town or on vacation — smile and say “hi,” but let him guide any further interaction from there. If he’s ready to wade into deeper waters with you, he’ll let you know … no text necessary.