From the Mailbag: Dating Women Who Dress Sexy

So, you’re dating a super hot chick who’s fun, easy to talk to, and gets along with your friends. The one thing you’re unsure about is the way she dresses. No matter where you go, other guys are constantly ogling her, undoubtedly undressing her with their eyeballs. She isn’t helping the situation much, as some of the outfits she chooses make it practically impossible not to notice. Remember the thing she wore to your buddy’s barbecue that got a lot of attention? It looked like her clothing got attacked by a shark before she put it on. Needless to say, your gut is telling you she is dressing too sexy, but you don’t know what to do.

This is a “rock and a hard place (no pun intended)” situation, because every guy wants to date a sexy girl, but that sexiness is creating some uneasiness for you. Why fault her for being the sexy girl you want to be with? Would you rather date an average looking woman that dresses conservatively who never gets looked at? Or how about an average looking woman who actually does dress sexy, but nobody really wants to see it, like someone you’d see in the “People of Walmart”? If shes hot, people are going to notice. She will turn heads. It’s something you need to live with if you do REALLY want to be with an attractive woman.

Now, the part about her wardrobe selection is another story. This is something well within her control. If shes beautiful and busty, she can decide to wear a top with a conservative neckline, or one with a plunging v-neck, to which every straight guy in her vicinity will feel his eyes being drawn to. Hell, it might not be just straight guys who look! She may get looks from other women, too. Her decision to draw attention to her God-given gifts is simply that; hers. The degree to which you should voice your opinion on it will depend on the type of relationship you are in, along with the setting in which you plan to spend time in. Let’s break it down.

If you’re in a serious relationship; i.e. long term, engaged, or married, you are absolutely within your rights to “say something”. You’ve built trust with her, you have shared goals, and you theoretically should be able to discuss all topics with each other. How you decide to approach this conversation and why her choice of clothing bothers you will be the most important factor of your conversation. We will examine this a bit later on.

If you’re casually dating, or it’s fairly new, you really don’t have a leg to stand on. This is not a situation where you make joint decisions, life choices, or are obligated to compromise on things. Think of it as “just fun”, and take it or leave it. If dating is about evaluating the long term feasibility of a partner, this concern is a mark against her.

Before you approach her on the topic, try to think about what it is that upsets you about the way she dresses. Consider the following ideas:

  • Do you get upset when other guys notice her?
  • Are you jealous of the attention she receives?
  • Are you worried someone will make a disrespectful comment, forcing you to “defend her honor”?
  • Do you think she may attract a man who is better than you?
  • Do you believe she isn’t classy because of what she chooses to wear?
  • Are you worried about what your friends and family will say?

Really think this through and understand which point(s) irk you most. What you’ll notice is some of the concerns tie back to your true feelings about her, while others are about your own insecurities. Either way, it’ll be revealing. If you’re concerned about guys disrespecting her and you know you’ll be forced to defend her honor, have that conversation. Ask her what she wants you to do if someone tells her she has a “nice ass” or if someone whistles at her. If she expects you to throw down every time it happens, you have a problem on your hands. She has to accept that scantily clad dress will deliver some disrespectful, unwanted attention. If it’s the acceptance by friends and family that worries you, remember this; they’re not the ones dating her, you are. If you’re okay with it and she makes you happy, that’s all that matters.

When you decide to have the conversation, rationally lay out why you feel the way you do, and ask her to consider these points before choosing what to wear. Do not try to tell her what she is allowed to wear, as this will backfire. Avoid calling her names and labeling her. Keep it focused on the what and the why. Her reaction to this conversation will tell you everything you need to know. She may not react agreeably in that moment, but give it a few weeks to see if she makes any adjustments. If she doesn’t change the way she dresses, it’s on you to decide whether or not it’s a dealbreaker.

Personally, I would never try to change the way a woman dresses. It’s not a conversation I’d want to have, and not a battle I’d pick to fight. Of course, if you’re attending a family or work function, it is within your purview to let her know what the dress code is. Your girl can’t expect to wear a low-cut cocktail dress to a funeral, or daisy dukes and a tank top to one of your work functions. That’s just basic etiquette, and she has to respect that. Outside of work and family of events, it’s not your place to tell her what to wear. Take it or leave it, this is who she is.

-Your Big Bro