Ask Natalie by Natalie Bencivenga

Girlfriend has terrible fashion sense and you aren’t sure how to tell her? Best friend going through a bad divorce and hooking up drunk? What should you do?

DEAR NATALIE: I love my girlfriend, but she is a terrible dresser. Every time we go out, she is either in sweatpants or puts together terrible outfits and looks ridiculous, like a kid playing dress-up. She has a great body, but never shows it off and she just doesn’t dress like the professional business owner that she is. We are supposed to go to a big client dinner for my work in the next week or so, and I am worried as to what she will wear to the event. Is there anyway to tell her that she looks bad and to get her new clothes without hurting her feelings? At this point, I would be willing to shell out a lot of money to buy her a new wardrobe. -WARDROBE MALFUNCTION

DEAR WARDROBE MALFUNCTION: Telling your girlfriend that she looks bad is probably not the line I would start with. Instead, why don’t you suggest a joint shopping trip and offer to buy her a new outfit for the client dinner? She may like that you are giving her a gift, and then might be more open to you picking something out. The other thing that may be going on here is that she simply doesn’t care about fashion or clothes or hates shopping. If this is the case, you may want to go out and select a few looks for her (in various sizes) to see what she likes. Have someone at a local boutique help you put something together and check her closet to see what size she normally wears in dresses and pants. Jeans are particularly tricky to fit, so steer clear of them. If she is not a “dress” person, try finding her a cool jumpsuit or a fun pair of pants with a couple of tops to choose from. But do not make this out to be like you are trying to change her. Instead, say something like, “I really appreciate the fact that you are going to take time out to attend this client dinner with me. I wanted to do something nice for you, so I picked out a few outfits for the occasion.” If she only likes one, save the receipts and return the rest. But who knows? Maybe she will like them all and keep them. Now you just have to find more fun places for her to wear them! If she acts insulted, tread lightly. She may honestly think that sweats are appropriate dinner attire and not get what the big deal is. If it comes to that, you may have to get a little more real with her. I hope for your sake that you don’t have to, but be prepared for her to bristle. In any case, remember that the woman you love is what counts, not what she wears to dinner. (But once again, sweats are just a bad look outside of the gym or living room!)

DEAR NATALIE: My friend recently got divorced and has been acting very self-destructive. Her husband had an affair and when he left, she fell apart. She has been having a lot of casual sex with random men and has been drunk most nights when going out to meet them. I am concerned because this is not in her nature. She was always the “good” girl. In fact, her husband was only the second man she had ever been with, and they got married at 21. She is now 30 and acting like a child. What should I do? She is my dear friend and I am worried for her. -- HOT MESS

DEAR HOT MESS: Sounds to me like she is making up for all the bad decisions most people get out of their system in their 20s. I wouldn’t pass so much judgement on her, if I were you, but I would encourage her to drink less. In fact, plan things outside of the bar, like going to the movies, to cultural events, to yoga in the park — whatever doesn’t revolve around drinking. She is probably drinking because she is incredibly sad about her marriage ending, and being cheated on compounds those feelings. She most likely feels betrayed, hurt, disillusioned and bad about herself. Doing things that are uplifting and focused on her, not on meeting new men, might make her feel more confident. There is nothing wrong with casual dating, but she needs to be safe and meeting men while she is intoxicated is a good way to make bad choices. If she continues drinking excessively, you may want to talk (gently!) to her about how wonderful she is, how powerful she is, and how this is a time for finding out more about herself. Dating is fun, but can be destructive in a time like this. She is entitled to enjoy herself and her new freedom, but encourage her to take a step back, slow down and think about what she wants to gain. She may be unaware at how this divorce is making her implode and a conversation with a BFF may be just what the doctor ordered.

Natalie's Networking Tip of the Week: Want people to invest in you and what you are doing? Make sure you are invested in other people. Think about the “we” and less about the “me.” This is a great way to expand your network and show people that you care about them. In return, they will care about you, too!

Please send your questions to Natalie Bencivenga to her email,; or through postal mail to Natalie Bencivenga, 358 North Shore Dr., Pittsburgh, PA 15212. Follow her on Twitter at @NBSeen and on Instagram @NatalieBenci

(This column was originally published by the Pittsburgh Post-Gazette.)