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He was the closest thing I ever had to a gay best friend until I moved to New York.  I could count on him to tell me if my outfit looked stupid, I had food in my teeth or if I was getting fat (as if).  His brutal honesty and good natured sincere advice are what make him who he is.  He’s my best guy friend.  (He’s straight, ladies- and single. He wanted me to make that crystal clear).  Here to tell you everything you always wanted to know, but never wanted to hear, Dr. DatedHer.

WDYWT: What are the clothing items that you wish ALL women would dispose of?

Dr. DatedHer: I wish all women would dispose of the following:

• Light colored jeans. They make you look fat.
• True Religion anything.
• Babydoll dresses (I don’t get it, they aren’t flattering, ever.)
• Fur coats
• Shoes with really chunky wedge heels (not sexy at all).

WDYWT: Wow, tell us how you really feel.  So, what do you love to see women wearing?

Dr. DatedHer: Daytime/casual- a hot pair of skinnies from Jean Shop with a pair of flats and plain and simple v-neck tee.

Nighttime- give me a chick in short black skirt, black top some jewelry, black stockings (the ones with the designs in them) and a legit pair of stilettos.  Boys love stiletto heels and being that this is NYC wear all black.  I find black to be incredibly sexy during the winter.

WDYWT: What is the BIGGEST mistake a girl can make on a first date?

Dr. DatedHer: Touching her phone. Seriously, I’m paying for your dinner. Put your f’ing phone down.  Finding out what happened on Rock of Love can wait an hour.  Think of it as a business dinner….you wouldn’t start bbm’ing/texting in front of your boss, show the same respect to whatever lucky boy you’re with that night.

Now, most guys are going to get mad at me for saying this but ladies, seriously don’t go home with a guy on the first date.  Make him work for it.  Don’t even kiss him.  Give him a hug and thank him.  If you like a guy, make him work for it.  Play the game properly.  There’s also a huge difference between playing the game properly (don’t give in too easily, don’t come off overly eager etc.) and the just being a bitch (actually being rude).

WDYWT: So what is a “dealbreaker” for you?

Dr. DatedHer: Another deal breaker/super annoying thing women are guilty of….not texting the next morning and saying, “thank you for a good time” (even if it wasn’t).  If it was tremendously bad, ok, I understand, but if the guy generally means well and picked up the bill…thank him.

WDYWT: I mentioned that you would tell me if I looked fat, but you wouldn’t really tell a girl that, would you?

Dr. DatedHer: When a girl asks if she looks fat in something, I typically tell a variation of the truth or suggest a different outfit. Simply saying, “Yes, you look fat” is NEVER a good idea.  As a rule of thumb, you can never say anything bad without adding a compliment.  So for example if asked, “Do I look fat in this?” I might answer, “Hmm, not sure if that’s the best look for tonight. Why don’t you put on that dress that I love you in.” Then explain that it compliments a particular part of her body better.

WDYWT: So who would you describe as your “ideal” woman and why?

Dr. DatedHer: I think most guys would agree with me that the ideal woman would be most like Natascha McElhone’s character on Californication.  She is ridiculously sexy and yet very natural.  My buddies and I have it narrowed down that the best girlfriends we’ve had all possessed a strong mix of knowledge in music, fashion, and the all the crazy things going on in the world.  It’s truly amazing that some women still think its ok to be clueless about the world. Seriously, pick up a paper and read it.  Even if its one of those free Metropapers.  Educate yourself a little.  Any decent, hard working, money making guy wont wife you up if all you can speak about is shitty reality TV and Desperate Housewives.  Men like women who can speak intelligently about a variety of subjects, so really educate yourself.

WDYWT: Very good advice. I think most men would second that.  So on to really important things, what’s your favorite part of a woman’s body?

Dr. DatedHer: Continuing with my Californication theme, in the words of Hank Moody, “I love women.  I have all of their albums.”  It’s a big mistake to think that all guys have a favorite body part.  With regard to the female body, men are pretty much all the same in our thinking.  We love flat butts, round butts, big butts and small butts. Big and small, perky and full boobs, we love them all. Same holds true for long legs, skinny legs and thick legs.  If given the opportunity, men will find something to love about a woman they are interested in. For me personally, it’s about all of those things but most importantly, it’s about the hip to stomach ratio.  Give me a flat stomach with some wide hips and I’m loving it.

WDYWT: Well, Thanks, Dr.  That was, um, informative.  Ladies, feel free to ask the Dr. ANYTHING you want and he will be sure to give you some of that brutal honesty.