Resolving two common dilemmas about date nights

February 27, 2020

Retail and online stores roll out new clothing options for you every spring. There are always new colors and prints to get excited about. Styles will change, and you may be excited to try a new look. All you have to do is peruse your choices and when you spot something you like, press the purchase button on your screen or pull out your credit card and get ready to feel refreshed.

It’s that easy…or is it?

Often women have concerns or issues they’re working on, and they feel hesitant about shopping or get stuck partway through their shopping adventure.

As I sit here at my computer on Valentine’s Day, I thought the question below would be a fun one to address to start. Many women share with me that this is an area of their wardrobe that is sorely lacking or neglected. As you can see there are often reasons why that is true!

Two Date Night Style Dilemmas Solved!

One woman shares: “I’m back in the dating scene and so out of touch about what would get me noticed. I read somewhere that I should wear bright colors, and another source said to tone it down so as not to appear too desperate. How much skin should I show and how much is too much? What do I do?”

This is a really big topic so let’s start by addressing two questions I’ve heard from women.

Dilemma #1: To bare or not to bare

Whether you’re back in the dating scene or just want to feel beautiful when you go out with your special person, the same advice applies.

A few years ago I spoke to a group of women who were attending a workshop on how to feel more confident re-entering the dating scene. One woman shyly raised her hand and asked me on which date should she show cleavage? From the reading she had been doing she ascertained that at some point she should show a little extra décolletage and she wanted to know when and how to do that.

The first thing that was obvious to me was that she felt extremely uncomfortable with showing any cleavage at all. She was trying so hard to do it ‘right’ according to handbooks she’d read, but clearly right for her had nothing to do with baring skin. It wouldn’t feel authentic or comfortable to her and she would definitely project this discomfort. Her embarrassment would make it hard for her date to truly get to know the real her OR for her to relax enough to enjoy her date.

We chatted for a bit and when she realized that she never needed to bare anything she didn’t want to, her relief was obvious!

There are many ways to look and feel special and sexy and for her, adding an alluring touch could come in her choice of soft fabrics that moved easily along her body or jewelry with a little extra sparkle or a dress in a drop dead gorgeous color that made her feel like a million bucks.

Dilemma #2: Is black too severe to wear on a date?

At the same dating event another women felt perplexed to the point that she avoided situations that had dating potential at all.

Her dilemma was about color.

She loves wearing black, but friends have told her it’s too severe for a date and that she’ll scare off any potential suitors. This advice made her feel so discouraged and confused. She wasn’t against wearing other colors, but black was a staple and she liked it and felt good wearing it.

She wondered what to do?

Let me start by saying this woman was tall and elegant and black looked very sophisticated on her. In fact, she looked stunning in it. Her fear, after a friend ambushed her, was that black made her look looked harsh and unapproachable which was definitely not the image she wanted to project.

She had tried wearing soft blues and even a hint of red, but she felt conspicuous and self-conscious. Somehow that doesn’t seem like very good energy to bring to a date whether a first encounter or out with a long-time spouse or even a fun evening out with girlfriends.

What we settled on was that she can definitely wear black because it looked great on her—maybe she’ll mix it up from time to time with other flattering colors, but black certainly wasn’t off limits as her friends suggested.

We also looked at how to soften the intensity of the black while still remaining true to who she is. A touch of lace here or there, silky fabrics that looked elegant and soft or jewelry that was pretty with a soft sparkle. These all allowed her to feel comfortable in her favorite color AND bring a feminine feel to her look that she enjoyed and made her feel special.

The bottom line in all of this is that the ‘right’ message is not about trying to second guess what will make someone else like you. The idea is not to attract random potential partners but to appeal to those who will enjoy who you are for who you are.

It’s about being so totally authentic that YOU feel amazing, self-confident and beautiful. That’s the energy that draws people to you and puts people at ease when they are around you! All because you are simply being you.

What’s dressing for date night like for you?

  • When you look in your closet do you find that the bulk of your wardrobe is made up of work clothes or hang around the house clothes?
  • When you try to get dressed to go somewhere other than work do you feel stuck with limited choices and, even after trying several things on, nothing feels right or special?

Some variation of these scenarios is something I have helped women with many times. When you look and feel fabulous you can relax and enjoy yourself. If you feel that your wardrobe and personal style could use a lift, let’s talk. I’ll be happy to share how we can make that happen so your date nights (or any occasion) feel delicious and fun!

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