“How Do I Tell My New Boyfriend About My Misdemeanor?”

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.


  1. Oh man “Living with regret” this sounds like something I would get myself into. Best of luck girl and totally just suggest Mexico 🙂 & probably he wont care about your prior misdemeanor its nothing too serious and PLUS if he cant love you/ like you for who you are and what has happened to you then you probably dont need him anyways. 🙂

  2. Great advice to the 2nd lady especially. Yikes, back off, fireball!

  3. Good rule of thumb: let’s all, as the human race, just assume from here on out that all text messages (and emails, and voicemails) are delivered and received. It’s so rare that they aren’t, and that tiny chance is always the first thing we stupidly cling to when something feels off.

    1. BeccaAnne says:

      Except when “Oh, no I never got that message from you, I totally wasn’t ignoring you”
      Not that I ever do that.

    2. TheFabulousmzm says:


      1. My phone has this handy function where I can tell it to notify me when the message is received by the other person. I do this for important texts sometimes, but my dad does it always. Might be something to consider.

      2. HelloJello says:

        Received or read? Or is that the same thing in this instance. My mother doesn’t have any such function on her 30 year old phone, but she assumes that texts are received and read the moment they are sent, and if you don’t respond, you get the ol’ “Hello? Hello?”

    3. Natasha Kingston says:

      Good call, this was another thing that made me laugh about that letter.

    4. Yes, congratulations, Wendy. This is fantastic!

      One comment about texts, emails, etc. being received: Wendy was dead-on about why these were ignored, and I agree that emails are delivered nearly 100% of the time, and texts as well – although texts _can_ be delayed at times… but very very very rarely.

      _However_ – and this is assuredly not the case with this gentleman – someone who gets a lot of email might miss one, especially from someone new. And someone who gets a lot of texts might overlook or forget or not recognize a number if they haven’t added it as your contact info. So for those of us who are e-connected, especially those of us with multiple email accounts and perhaps more than one cellular number, it’s not impossible to innocently not notice or remember an email or text.

      But even that is still rare.

      1. There he is. I hope you’ll be as prolific a commenter here as you have been on TF, jsw.

      2. I’ll try… it’ll be harder here because I won’t have all the easy targets to mock. 😉 Your writing is too hard to disagree with.

  4. Um, Wow LW2-
    Is it really in your best interest to even consider dating the Widower of a former patient? You did not specifiy in what capacity the deceased wife was a patient, be it that you were her medical provider, massuese- or god forbid Therapist! – point being, does it reflect well upon you professionally to be so actively persuing the spouse? Is it worth the risk of your professionalism to be super stalking a man who clearly seems not to be ready/or into you?

    1. I was thinking the same thing about dating an ex-patient’s spouse. I am not to sure about that.

  5. BeccaAnne says:

    LW1- Totally not something you should be ashamed about. Go ahead and tell him.
    LW2- too strong.

    1. LW1 – when it comes down to it, it’s just a misdemeanor so ultimately no biggie. I think Wendy’s right – you might need to look into the border rules more closely. But either way, if you think this is going somewhere with the guy and it’s really bothering you, just tell him the story. It’s not that bad – you were doing what you thought was a good thing at the time – it’s not like you got busted snorting lines off the barrel of an AK.

      LW2 – I feel so badly for you in this. I agree with Wendy – it was just a little too much too fast. He was clearly deliberating over the whole thing since it took so long for him to come by and ask you out. He must like you a lot, actually, to want to take that step. With it being the holidays, I’m sure the memories were just too fresh. I’m guessing you may hear from him again one day – and if not, oh well – awkwardness dodged.

      Congrats on the new site, Wendy!

    2. Sorry, BA – meant for this to be a general comment. 🙁

      1. BeccaAnne says:

        Haha, it’s cool LJ. I was a little excited someone replied to me. 😛

  6. heidikins says:

    Oh man, Living with Regret, I think we’ve all done the dumb thing with a previous flame and are still paying consequences. The really exciting thing, is that you’ve been dating less than a month and he wants to take a trip to Canada! Weekend getaway? He sounds like he’s in to you–I’m sure he’ll understand about “that one thing that one time with the weed…”

    Totally Baffled, I think there was a very popular book and subsequent movie about this very topic. If he’s interested and ready, he’ll call. If not, your multiple attempts are just gonna freak him out.

    Excellent debut column, Wendy!

  7. For both…Wendy gives good advice. I feel like I say this a lot. =D

    But seriously, spot on for both…but for LW2, I’d like to add, he’s also probably now feeling GUILTY for asking out his late wife’s health care provider(?) right before the holidays, a year after her death. Not just the guilt from moving on, but that he’s moving on with someone who was a major part of his late wife’s life, especially near the end…I don’t know, but in his shoes, I’d imagine that I’d be questioning what made me ask you out, and whether I had been having these thoughts even before July, and trying to figure out exactly how disloyal I was being.

    Give him a break…if it’s more than just a passing chemistry, he’ll likely contact you when he’s ready. If not…well, that’s your answer right there.

  8. banana_hammock says:

    I would not not not suggest mexico. Unless you want to be shot by some drug cartell. it is certainly not lovely this time of year!

    LW1 Just tell him already. Chances are he too has some things in his past he isnt proud of. Afterall, no one is perfect, we have all done things we arent proud of. Your honesty could help strengthen your bond

    1. BeccaAnne says:

      there are plenty of safe _beautiful_ places in Mexico.

  9. spaceboy761 says:

    LW2- This was a touchy situation to begin with and you just came on too strong. A guy in his position should get all of the space he needs.

  10. LW1: If your new guy is really caring and a good guy, then he shouldn’t care about a stupid mistake you made in the past with accepting blame for the misdemeanor.

  11. vizslalvr says:

    LW1 – Just tell him! If he’s not okay with something as small as that, he’s not a very accepting person and I would seriously reconsider being in a relationship with someone like that. You need to be able to share things with a potential partner.

    My brother has an OVI (similar to a DUI) and because you cannot get that expunged from your record in the state we live in, he’s never going to be able to go to Canada again. Ironic, since that’s where he bought his first fake ID … Annnnyway, I don’t doubt that it’s impossible for her to get into Canada. We had a layover in Canada on a family trip to Europe this past May and he needed special permission and an escort just to go from one plane to the other.

  12. Natasha Kingston says:

    Wow, LW2, even as I was reading that you sent a second text I was thinking, “Pull back, Pull back!” Definitely too much too fast for a man that is getting over a loss like that, especially if it took him several months just to come to your office and ask you out.

    1. Me too! I’m not sure if the second text was even needed. I like just laying low and having a man pursue me. Makes me feel special. 🙂

  13. Jess of CityGirlsWorld.com says:

    Congrats on your debut Wendy! And great advice all around. I cringed reading LW2 because we’ve all been there at times. But “mirroring” is always a wise course in situations like this….

  14. ArtsyGirl says:

    Yay for Wendy’s new site! I am looking forward to getting my daily dose of amusing letters and spot on advice.

    LW1: It sucks to have to rehash past mistakes, especially ones that involve the legal system. Here would be my rule of thumb, it is not something you need to parade out every date you ever go one, but when you get into a relationship it is something to calmly sit down and discuss with your SO because it can affect your relationship (i.e. traveling to Canada). Like Wendy said, just calmly sit down and explain it like you did in your letter. It contains all the relevant information without any mess. I am sure he would understand especially since we have left the destructive relationship and are trying to learn from your past mistakes.

    LW2: I am sorry that this relationship is not proceeding as smoothly as you would like. One of my friend’s widowed mothers is just getting back into the dating game. She is feeling a lot of tension and stress and her husband passed away over a decade before. I can only imagine what this guy is going through after just 1 year! It is apparent that you are really interested in the guy but I imagine that if you want a ‘normal’ speed relationship you should move on. A widower is facing a lot more hurdles than a single or divorced man since there is a lot of (unnecessary) guilt and anxiety of dating after possibly decades of marriage. Follow Wendy’s advice and back off to give him space. I would remove him from your bulk text list and wait for him to contact you. If it doesn’t happen, let it be, but I will keep my fingers crossed for you.

  15. Wendy! This is my first time reading your column- now that you’ve gone rogue!- no SP reference. I love your advice. Another reader said “spot on.” I totally agree- and so helpful: I can’t believe you checked out her Canadian travel potential- of course she can get into Canada. I thoroughly enjoyed your guidance. I think most folks can use some behavioral correcting and you are clearly the woman for the job.
    Good luck with the new site!

    1. You are going to enjoy this site. I am impress with Wendy too. I agree with her most of the time. I am usually the one among my family, friends, and co-workers who doles out the advice (I think I encoourage them to see different options or solutions to different situations). I am too busy growing and getting to know who I am to give advise on a regular basis. But Wendy is pretty good. Enough, let the blogging continue.

  16. LW2: You definitely came on too strong, like Wendy suggested. I completely feel for you, though. I know I’ve been in the situation where you’re just desperately waiting for that special someone to respond, and it’s such a big hit to the ego when they don’t. Next time just cut your losses and move on.

  17. fallonthecity says:

    First column on your new site! I’m excited to keep reading.

    For LW1, the first thing that came to mind was, ugh, what concert — Bonnaroo? Every year, the cops in my home town (in TN near-ish the venue) seem to work overtime to intercept concert-goers on the drive up and make all the drug busts they can. I mean, you should see the “arrests” section of the paper that week. Anyway, LW, your new boyfriend will understand. Everybody has done dumb crap for dumb SO’s. Live and learn, right?

  18. TheOtherMe says:

    LW1 : As Wendy said, just tell him the same was you wrote it, I can only speak for myself but I could only feel sympathy for you.

    LW2: Maybe, just maybe it was a little much but you had the right to want to follow up when he was the one who initiated the contact, he was the one who came to your office, he was the one who asked you out. It would have been totally acceptable for him to just let you know if things were moving too fast, unfortunately it often hurts more to be completely shut out than to be told the truth.

  19. Anne (I Go To 11) says:

    LW1: I agree with Wendy and everyone else. Just talk to him. 🙂

    LW2: It’s possible he pulled a disappearing act because he felt overwhelmed, both by his grief and by your pushing things. One of my best friends died in a car accident 5 years ago. (He was like a brother to me, and it took me an entire year to finally come to terms with him being gone.) Right before the accident, I’d just started a flirtation with a guy. Within a couple weeks after my friend’s death, this guy kept trying to push dating, and I was in no state of mind to even consider dating anyone at that time. It just got to be too much, so I ignored his calls, blocked his chat screen name, unfriended him on MySpace, and tried to cut off all contact because I felt suffocated. Now, if my friend hadn’t just died, I would’ve been up front with the guy about not wanting to move forward instead of trying to ignore him, but being consumed by grief changes the game entirely. (The guy wound up going off on me about ignoring him, calling me immature and selfish and a few other things, so in the end I dodged a bullet.)

    So to echo everyone else, CALM DOWN. You don’t know where he is in processing his grief, and it could backfire on you. If he’s truly ready to move forward, he’ll let you know.

  20. fast eddie says:

    Much as respect Wendy, I disagree with her on LW2. Assuming this guy’s got keeper qualities and yours are up to snuff, bear in mind the adage “She who hesitates is lost”.

    The first months after I lost a lady love to pneumonia there were several single women in our circle of friends that put some effort into consoling me. It was helpful and a bit overwhelming. He’s still in morning and it will take a while to come to grips with where to go from here. I think you both would benefit if you took the infinitive to make contact if for no other reason then to be a supportive friend.

    1. WatersEdge says:

      I disagree- I don’t think he wants to be friends with her. It seems like he thought that he wanted to date her, but now he doesn’t. I think that it would be totally inappropriate to continue to approach someone when they have a 0% response rate. If he is still interested, he’ll contact her again someday.

      1. HelloJello says:

        I agree with WatersEdge. He’s obviously, for one reason or another, not up to communicating with her at this point. Another uninvited text or email at this point might actually creep him out.

  21. Mexico may be beautiful this time of year, but is it *safe*? 😉

    Like others have said, LW2 was kind of cringe worthy. I probably would have even done the same thing if I were in her place, but sometimes it takes an outsider looking in to say, “AH! TOO STRONG!”

  22. Kaiser Söze says:

    LW2; solid points made by Wendy.

    Could it also be that the LW herself is perhaps not in a place to be “mingling” with an emotionally fragile potential romantic interest?
    Perhaps she got a little too excited, which is okay – you won’t be the 1st or the last to err due to a little excitedness.

    Assuming he re-establishes contact, you’ll have to do more to keep your emotions and romantic expectations in check to provide a platonic and safe but cautious ground to grieve and heal before you awaken any romantic interests that may lie between the two of you.

    Reckon it might be a tough and slippery road so tread carefully.

  23. ReadingIsFundamental says:

    LW2: Mixing with patient family is just a big old mess. Don’t go there. You know full well that after a death the family members are very vulnerable and as an authority figure it’s a bad plan to mix business and pleasure. That’s without considering the legal risk — if things don’t work out but it’s still within the statute of limitations for malpractice in your jurisdiction that person or some other vengeful family member can manufacture a suit, regardless of the facts.

    I would go so far as to call it unethical but YMMV.

  24. So happy for you, Wendy!

    @LW1: Unless your new guy’s super uptight, I don’t think it’ll really bother him. And, I second what Wendy said: Do a little further investigation to make sure you really can’t get into Canada.

    @LW2: There’s no way around this… you came off as stalkerish. We’ve all been there, and the only thing to do is cease contact unless he happens to reach out to you.

  25. Hi Wendy! I’m a huge fan of yours on TF and am so excited for you and your new website!!

    LW1 – I’m agreeing with everyone…just tell him. It doesn’t sound like a big deal to me.

    LW2 – I tend to come on too agressive as well so I certainly understand that you didn’t mean to and you were probably just letting him know you were thinking of him. I have to say though that Wendy’s advice about “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” is definitely something that should be followed! Thanks Wendy for giving some great advice everyone can use!

  26. LW1: If the record is due exactly b/c of what you described he should be understanding of it.

    LW2: Yikes. You def went overboard. And then made excuses to text him further. “Maybe he didn’t get my texts?” – I’m not saying that’s the case here but it reminded me of the book “He’s just not that into you” for the simple fact that you made an excuse as to why he wasn’t communicating w/you.

  27. Just be honest and present it the way you did here and never let anyone put you in that position again. Thank God it was a misdemeanor and they didn’t throw a felony at you, I know of someone whom took the rap for a “friend” and they got a felony conviction and can only work $8/hour jobs for the rest of their life and they have no money or health insurance and a really miserable existence. It upsets me he took advantage of you like this and now you are suffering for his mistake. Sounds like you are better off without him, with friends like that who needs enemies as they say.

  28. Calliopedork says:

    Totally agree with the advice for lw1, ive known if people with minor misdemeanors who have had exceptions made. Also your bf will orob find it funny.

    Congrats wendy, im crazy excited about the if theyd asked column I have always wanted to advise celebs

  29. bitter gay mark says:

    Wow, LW1…I simply can’t imagine being so in love with a convicted felon that I agreed to take the rap for his drug problems… Talk about about a bad, bad idea. Hope this is a good lesson out there to others who might be inclined to do the same… Yikes! What a mess. Sorry about your troubles. I agree, you have to tell the new guy all about this. Maybe he will be cool. Maybe he won’t… Truth be told, if somebody came to me with this story, I’d probably be “Oh, c’mon. Just admit the pot was yours, this whole did it for love thing is so made up!” But then again, maybe that’s just me and my own bias as I simply can’t imagine doing anything as STUPID as pleading guilty to a criminal charge to “save” somebody else.

    LW2… Yikes…back off, girl! You sound incredibly insensitive. The guy is going through the holidays…THE HOLIDAYS!!!!!! Which must really dredge up all the emptiness of his grief and magnify his genuine sense of loss and you just expect him to be chomping at the bit to date you —- somebody who will no doubt CONSTANTLY remind him of his deceased wife? Could you possibly be any more clueless? Or tactless? Stop sending texts already! (In the thousands of texts I’ve sent — I use them A LOT for work — I don’t ever even recall so much as one gong missing FYI…) Back off, LW2. Back off… What next? A cheery missive that states…. “Look on the bright side! Your wife may be gone — but ain’t it sweet how she brought us together!” I know, I know, surely I am way over the top by going here like this… But frankly, your nonstop stream of texts is already VERY over the top… Time to give it a rest. You are coming across as well beyond desperate here…. And desperation is NEVER attractive.

  30. I’m no border patrol official…but whenever we go to Canada, they don’t require us to even show a valid passport. A birth certificate and DL will do most of the time. We don’t have any criminal records, but we did go up a couple times without passports and had no problems. The U.S. officials are worse about it, actually.

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