Photo Credit: Jewish Press

Dear Dating Coach,

I am not a fashionista. I rarely dress up, I’m not into makeup, and feel most like myself when I’m dressed casually. I find it frustrating that I am forced to be “fancy” for dates, when I am a ponytail and sweatshirt kind of girl. Frankly, I think it is inauthentic to pretend I am something that I’m not. My family however is less than impressed with my attitude and completely disagrees with my viewpoint. Please tell them to back off and let me be me!


Hopeful Hoodie


Dear Hoodie,

Everybody loves a buffet. Where endless choices and elastic waistbands coexist and cater to every appetite. In our house, we love a quiet Friday night buffet. A no guest, no frills excuse to line up our 9 X 13’s and pick and choose straight from the kitchen counter. Yet, when our table is lucky enough to be graced with guests (especially new guests), we shed the shmorg for pretty presentation instead. We carefully arrange platters, beautiful boards, and delicate bowls for them to enjoy. Every garnish, arrangement, and artfully prepared tray reminds our guests that we are excited to have them at our table. Sure, the chicken might have been sampled in foil at our evening buffet, but it is certainly elevated by my grandmother’s heirloom plate. The recipes don’t change from buffet to platter, but the message is altered in preparation. Having new guests is special, and a special tablescape tells them so.


I Would Stop…

You are a casual gal and you are happiest in your sweats. We hear you and we feel you. You dislike dressing up and go as far as to imply that you would be misleading your date with your fancier look. If you are not generally dressed up you feel it is dishonest to present yourself in a way that differs from your usual look. Your family however, disagrees with you and this has become a frustrating sticking point for all of you.


Buying Makeup…

Sure, there are those that love an excuse to pull out their highest heels for a special evening out and there are those who think Chapstick is pulling out the stops. We are all unique in our tastes and appreciation for clothing and style. There is nothing wrong with being someone who prefers denim over lace, and there are many instances when a casual look is the definite way to go.


But I’m Not…

Be that as it may, a date is a special event. When we dress up for our date, we are conveying our care and interest in the outcome. Every minute you spend on selecting a beautiful outfit, doing your hair, and applying tasteful makeup shows your date that you are excited to meet him, to get to know him, and to connect. The attention that you put into your appearance clearly states your level of interest. If your clothes could talk, the hoodie might say, “I can’t be bothered, I’m tired, (or worse), let’s get this over with.” While your carefully put together outfit tells your date that you took care especially for him. This is an instant indicator to him that you are eager and enthusiastic. (Of course, should things progress and a more casual date calls for a more relaxed look, that would be appropriate; though still with thoughtfulness.)


A Quitter.

It is not inauthentic to dress up. It is respectful, smart, and direct. Showcase your interest and your enthusiasm with a thoughtful look and your date will notice, reminding him in turn to put his best foot forward in all aspects of your potential connection. It’s ok to be a hoodie temporarily gilded on a fancy platter. You are still you, with a hint of fairy dust and shimmer.


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Henni Halberstam is a Dating and Marriage Coach whose expert advice will help you navigate dating and relationships in order to ensure a successful marriage. You can contact her at to schedule a phone session.