Dear Sangita: I recently discovered that my boyfriend has been a cheater in every single one of his past relationships … and always with the same person. The problem is that person is going to be in his life forever — it’s his childhood best friend. He says it’s not a problem anymore, that he’s changed and that I’m “the one.” But what if he said that in all of his past relationships? — Once a cheater?
Dear Once: It doesn’t sound like this woman is someone you want in your life, and the same probably goes for your boyfriend. Is this guy worth it? Is this the one you want to invest in? You have to ask those questions. And ultimately it’s not going to be about him, it’s going to be about you. If you’ll continue to feel jealous throughout the relationship, you’ll be the one who has to sit with that. To me it sounds like this woman has such a hold on him that he might not necessarily want to be a cheater, but he’s in this vicious cycle.
This may sound ridiculous, but I would ask her yourself. Say, “I really like this guy. I want to make it work. What are your intentions here?” If she really cares for him, she’ll take that to heart. But if she tells you that she and your boyfriend are supposed to be for life, take it or leave it, then you can save yourself the heartbreak of investing in this guy.
Dear Sangita: I lent my friend a lot of money after they said it was an emergency — and now they’re on vacation, posting lobster dinners. Do I ask for the money back or take the loss … or cut ties? — Lending regrets
Dear Lending: I would personally say cut your losses. I know it’s scary to ask for money back, because you think it will affect the relationship. So if you want a gentler way to bring this up in the conversation, you can ask, “Hey, that money that I gave you, how did it work out?” The mistake we sometimes make is to lend money without saying, “Hey, pay it back in six months.” With an open deadline, people will forget — or take advantage. So it might work to give a generous deadline during this conversation, giving your friend plenty of time to pay you back but gently reminding them they still owe you.
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