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Dear Wendy: The Ex Files

I have been dating my man for a year and half and we have been living together for five months now. All in all, we have a great relationship, however, I worry about his feelings towards his ex. He has all of their old emails saved on his computer and I did some snooping (I know, I know, asking for trouble) and discovered that they had a flirtatious relationship up until we had been together for three months. She texted him frequently when she was drunk; they said “I love you” to each other; and he even called her on our first Valentine’s day together as a couple. He was honest about speaking with her, but was not honest about the extent of these exchanges. Furthermore, why does he still hold onto these emails? He also has a bracelet she gave him that he swears he will never part with (even though it’s metal and scratches me sometimes when we have sex). He feels that asking him to let go of these reminders of her is unfair. She was the first person he slept with and he’s a loyal guy, so I understand that his “sentimentality” was a contributing factor in all of this. Their last contact was over a year ago, though, so should I just let it go? Or should I admit to snooping and discuss it with him? Does this sound like bad news to anyone but me?? — Suspicious

Whether your boyfriend’s ex was his first serious girlfriend or not, he has every right to be sentimental about his relationship, just as we all do about any parts of our past. The relationship is a part of his history and what helped make him the man you love today. I love my husband with my whole heart and couldn’t imagine being with anyone else, but I still keep a few relics from previous relationships — some photos, a few love notes, stuff like that. They’re boxed up in the bottom of some drawer and I never look at them, but I’d be pissed if my husband expected me to throw them away (although I would if it really upset him that much). They’re like the old high school T-shirt I hang on to and the mixed tape my roommate and I made freshman year of college — they remind me of where I’ve come and how much I’ve grown.

That said, emails saved in some folder or notes filed in the bottom of a drawer are one thing; a bracelet that your boyfriend wears on a regular basis — one that scratches you during sex! — is something else altogether. It’s not just inappropriate for him to continue wearing it, it’s a real slap in your face. Let him know how much it hurts you that he continues to wear a piece of jewelry — something that’s probably quite personal — from an ex-girlfriend. Tell him you’d be happy to replace it with something from you, and that you don’t expect him to get rid of it, but you’d appreciate it if he quit wearing it and kept it in a drawer or some place where you didn’t have to see it all the time.

As for the information you found while snooping, I’d let it drop. If the last contact your boyfriend had with his ex was over a year ago, you’d just be dredging up old stuff at this point for no good reason. I’m sure it stings a little that he was still exchanging intimate messages with her after you’d started dating, but it sounds like you weren’t very serious with him yet and he has long since stopped talking to her. Let it go. And accept that we all have pasts — we all have people we loved or liked before ending up with the person we’ll be with forever. We can’t erase those experiences, nor should we.

I started dating my current boyfriend six months ago after he and I had been friends for six years. Everything is going great, except for the fact that he has a wife. In September of last year, they split after a year of marriage when she cheated on him twice. They have no legal separation agreement, and he is adverse to even talking to an attorney about the situation. She still tries to insert herself into his life (texting him, calling him, leaving messages on his Facebook), but he assures me he has no interest in getting back together with her even though he continues to indulge her. I am unsure if he really wants to be with me when he’s not ready to resolve the issues of his past relationship. Is it too early to have a talk about what’s going on with our relationship? Is it too forward to inquire about his previous relationship, and, if so, what are some good ways to approach the conversation with him? — Married Man’s Girlfriend

Is it too early to have a talk with your boyfriend of six moths about his wife? Um, no. It wouldn’t have been too early to talk about his wife on your first date! This isn’t a question about an ex he’s no longer associated with; this is someone to whom he’s still married! You have every right — and reason — to inquire about the status of their marriage: why it didn’t work out and when they plan to divorce. If he can’t give concrete answers to your questions and doesn’t begin taking steps to legally separate from his wife — or provide reasonable justification for not taking those steps — you should quit dating him until he is emotionally available for a new relationship.

Email me at dearwendy@thefrisky.com

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