Every time my ex gets drunk he send me the really awful, heart-wrenching text messages about how he misses me and how we should be together.  We’ve been broken up for six months.  I am not trying to be rude, but how do I get him to leave me alone? --Ren

The next time Romeo sends you a tequila fueled love letter don’t respond. Later, when he’s most likely sobered to his senses, send him a text explaining this can’t go on. You get him to leave you alone by TELLING him to leave you alone. If you haven’t explicitly stated that you will never, ever be getting back together, you need to do so. NOW. If that doesn’t work, change your phone number or put up with an annoying text every so often. I’m sure it’s not the first one you’ve received. Careful what you wish for. Some girls don’t get texts at all.  

I did the classic woeful tale of getting a tad too tipsy at our holiday office party and ended up making out with a handsome accountant from another department.  One, everyone saw it/knows about it.  Two, I’ve barely said two words to this guy in my life.  How do I fix this mess? --Sloppy

Sloppy, get over it.  No one’s talking about you any more. Oh, sure they did, but it’s January and they’ve moved on to resolutions, diets, and the latest Bachelor episode.  

There’s nothing to fix. You became a cliché. Look at the bright side though. At least it’s not a “Are you the Daddy/Jerry Springer” kind of cliché.  

I’m 27, single, and was introduced to this beautiful woman by mutual friends. Here’s the kicker: I slept with this woman’s younger sister for a brief stint in high school. I don’t think she knows—yet—but I do. I’d like to ask her out to dinner, and possibly address the past. Any advice would be appreciated. --Mike

Mike, you have to come clean before any date occurs. In this situation, better to be forthcoming and lose her now than to move forward, have her find out, and throw a drink in your face. (Or worse.)

I have a younger sister I know she would not be keen on me dating someone she “used to know”.  I, on the other hand, would have no problem with it.

This is probably something the sisters will need to talk over before you’ll be able to get the green light.  Good luck and here’s to many awkward family gatherings in your future.

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 weekly dating advice column, The Naked Truth, appears exclusively in Boca Raton Magazine. Her work appears regularly on the Huffington Post, and she has been a guest contributor to Shape Magazine, GalTime.com, Think Magazine, Blindfold Magazine, and more.  She can been seen on MTV’s Made and Bravo’s hit show, Millionaire Matchmaker in early 2013. 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, facebook.com/EssentiallyAngela or Twitter, @essentiallyang.