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Ask Lisi: We took a break and I had a fling. Should I tell him?

My boyfriend and I went our separate ways this summer since we were working on opposite sides of the country. Now he says he loves me. Should I tell him the truth about my fling?
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Lisi Tesher, for Ask Ellie column

Dear Lisi: My boyfriend and I went our separate ways this summer. Not due to the end of the relationship, but because we had both made commitments to jobs on opposite sides of the country, and we wanted to keep them. We are both outdoor nature lovers and are both getting degrees in outdoor education.

I was offered an opportunity to be a guide at a whitewater kayak centre in California, and he was offered a canoe trip guide position at the Northern Forest Canoe Trail in New England. Literally across the country from each other.

We thought it would be mature and wise to break up while we were apart, just in case we met someone else, or something “happened” with someone else. But we stayed in touch, messaging mostly, due to the time difference.

There’s a week left in both our contracts. He’s just called to invite me to join him for a hike (somewhere in the middle) for a week before we go home. He told me he loves me, and NOTHING happened all summer between him and anyone.

I was CONVINCED that he would have gotten together with someone, so…. I had a fling. It was mostly meaningless, but fun. Nice guy. Now I don’t know what to do. Should I tell my boyfriend the truth? Or sweep it under the rug? I know he’ll never find out.

Secrets and Lies

Do NOT sweep this under the rug. If you still love your boyfriend and want to get back together now that the summer is over, you MUST tell him the truth. Say yes to the hike, fly out and meet him, and run into his loving arms. Tell him how much you missed him, and how much you love him.

And then tell him the truth, and why you did what you did. He won’t be happy; he may have a very angry reaction and he may initially push you away. Be patient, loving and understanding. He’ll be hurt. But I believe that with honesty you can overcome adversity — hopefully together.

Dear Lisi: My sister showed up at my door, unannounced, about two weeks ago. I was thrilled to see her as she had been overseas for six months. I live in another state from where we grew up, for my current job, so I wasn’t sure when we would see each other.

She slept a lot the first few days and blamed it on jet lag. I didn’t think anything of it. She ate everything in sight, but she’s always been a good eater and super fit, so again, I didn’t think about it.

But then I accidentally walked in on her getting out of the shower…… she’s pregnant! She hasn’t told our parents because she doesn’t know what to do. She hadn’t even been to a doctor! I’ve since taken her, and she’s too far gone to terminate the pregnancy, even if she wanted to.

I’m happy for her to stay with me and figure things out, but she’s not saying who the father is, and she still hasn’t told our parents she’s back in the country. I need her to say something because I can’t pretend any longer.

Sisters’ Secrets

This is your sister’s secret to share with your parents, not yours. But I do understand that you are, for the moment, caught in the middle. Offer your sister your support any way she needs – by sitting with her when she tells them, by running interference after she tells them - however she sees fit.

But it is imperative that she tell them as soon as possible and get their support.

FEEDBACK Regarding the woman judging her wealthy acquaintance (July 17):

Reader – “Wow, you came down hard. In times of financial stress, job insecurity and hardship, it can be difficult to contain resentment. But I agree that she needs to stay in her own lane and stop spouting judgment of others in better economic circumstances.”

Lisi – Maybe hard, but hopefully she’ll mind her own business.

FEEDBACK Regarding the kid who got his ear pierced (July 8):

Reader – “The kid probably did it without the other mom knowing. Plus, if the 15-year-old is ONLY rebelling with an earring, she should count herself lucky. One more year and he is (likely) of the age of consent and can drive a car. That mom not only has to let it go but she must let him go. She either did a good job parenting or she did not, but it is now 95 per cent out of her hands.”

Lisi Tesher is an advice columnist based in Toronto. Send your relationship questions to [email protected].