Caroline from Ottawa asks… 

I’m a bit overweight; I don’t want to wear any tight dresses or high heels on a date. What can I wear so I don’t look like a wannabe? I hate feeling so exposed in anything tight so please don’t recommend a little black dress.

Hi Caroline,

You definitely don’t need to wear anything tight, but please don’t make the mistake many women do, which is wearing baggy clothes to try to hide extra pounds. You have curves, and men love them, so show them off!

I suggest you look in your closet and see which clothes make you feel good.

What is it about them? Color, style, fabric? You want to wear those clothes on a date. When you feel good, you radiate happiness and confidence, and those attract men like nothing else. And when you’re wearing clothes you don’t love, your entire attitude changes. You’ll have a vibe that doesn’t present who you are at your best.

If you’re hiding behind clothes that are too big, or you can’t pinpoint clothes you love, it’s probably time to go shopping. Take your most supportive girlfriend and a male buddy. You’ll have the best of both worlds: a girlfriend to help you pick out nice clothes, and a guy to tell you what men like. Trust them to choose two or three outfits for you and see what happens!

Men like heels, but you don’t have to go crazy with it. Many women feel more feminine when they have on shoes with just a slight heel, one or two inches. Something about the way women walk in heels makes guys notice. If you’re not comfortable with them, don’t wear them, but maybe a shorter heel will work for you. You’ll never know ’til you try.

Big hugs and good luck!
Jonathon