What are the rules for breaking up with someone—and then dating their friend? I did the breaking up, and I'm trying to figure out whether or not to discuss this with my ex. Or should I just let him find out as events unfold? —Don't Judge Me in Boca

Sorry but I’m judging you. You broke this guy’s heart, and now you want to add insult to injury by dating his friend. It’s a terrible idea, not to mention it’s just wrong. I'm pretty open minded, and you won’t find me standing on moral high ground often, but this is one of those instances that I’m standing on the mountain top and furiously waiving the red flag.

I know what’s going to happen already, and there is little use in me attempting to talk you out of it. My guess is that your feelings for the bestie played into the break up. If an advice columnist that’s never met you before can super sleuth this one, don’t think for one moment that your ex won’t realize sparks were flying while he was still your man.

Here's how this is going to play out. Expect your new guy to get a sucker punch to the face from his former best friend when you two lovebirds are at the bar. Don’t say I didn’t warn you. Oh, and here’s the thing. They will eventually get over this and become friends again—but neither will ever trust you. Bros before sneaky girls.


Hi Angela! I'm going to college in California and in a long-distance relationship with my high school sweetheart back here in Boca. It's not going well. He's wildly jealous. I'm completely faithful; I'm crazy about him. But his jealousy is driving me crazy. Help me, Angela! —Confused in Calif.

Dear Confused: A relationship does not have a good forecast if there is an intense undercurrent of jealousy from one or both partners. In a long-distance relationship, odds are bleaker. The jealous party eventually creates so much friction that even if you aren’t doing anything wrong, the assumption of guilt becomes too much. At some point, you either will act out as your jealous partner feared or you will break up to get relief from the accusations. If you want this long-distance college/high school relationship to continue, sit your boyfriend down for a serious conversation. Tell him you will accept no more jealous behavior or accusations. You are entering college. where you will have new friends and new experiences that he won’t be experiencing. He needs to understand that up front.

I don’t want to discourage you from staying in this relationship, but heed my words: This will not be an easy road, Confused. I want you to strongly consider doing the mature thing and giving each other the time and space to experience this exciting phase of both your lives without pining away for the other. This doesn’t mean you are done forever. You are just taking a break. If you are meant to be together, take it from someone who’s seen it all personally and professionally, you will find each other again.

“Jealousy. The dragon that slays love under the pretense of keeping it alive.” —Ellis


Do you have a question for Angela? E-mail NakedTruth@bocamag.com!

About Angela Lutin:
Angela Lutin is Essentially Angela. Blogger, Advice Columnist and Dating Guru for the social media age—decoding modern love one tweet, text, and like at a time. Angela’s dating advice column, "The Naked Truth," appears exclusively each week on bocamag.com and in each issue of Boca Ratonmagazine. Her work appears regularly on the Huffington Post. She can been seen on MTV’s "Made" and Bravo’s hit show, "Millionaire Matchmaker." Crafting personal dating makeovers for her clients, Angela also maintains a private practice, which turns the romantically challenged into the relationship-inclined. Follow Angela on Facebook or Twitter.