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Dear Dating Coach,

The last guy I went out with looked like he just rolled out of bed. I don’t think you need to wear a suit or even a dress shirt every time you go out, but this was too much! He literally put in zero effort and it made the whole date feel like he couldn’t care less. I actually thought he was a good guy but really struggled to get passed his “look.” Is it too much to ask that a guy doesn’t show up to a date in slides?!




Dear Bedhead,

We had a lot of guests last week for a Shabbos meal. I planned the menu, shopped for the right products and made sure the cloth napkins were ironed. On Shabbos morning, I decided it all seemed like too much work, so I just told my guests that they should help themselves. Grab a paper plate, open the fridge, pass the salt, and enjoy. No need for a tablescape or pretty dishes. No need to have flowers or platters for the food. Just grab some whatever, use your hands, don’t be shy, and plop some cholent on your plate. Sit on the couch, the floor, or just lean against the wall. The important thing is that they came and ate right? It was such a special and meaningful meal. NOT. THIS DID NOT HAPPEN. (Duh!) It would be difficult to participate fully in a meal so haphazardly offered. It would not make my guests feel appreciated or welcome. Unless you believe that old adage, “We eat with our eyes blindfolded.” Yeah, I don’t either.


If You Look Good…

It is frustrating to feel like an afterthought. While I would like to give your date the benefit of the doubt and assume he most certainly wanted to be there, how he presented himself made you feel otherwise. A sloppy appearance demonstrated a lack of care, you thought. He could not even be bothered to put on proper shoes, and his general clothing choices looked better suited for outdoor chores than a date. You concede that there is certainly space for “casual” in dating, but this felt like disinterest to you. You took the time to look presentable and nice for your date and felt that your date should have reciprocated in kind. Instead, he showed up unkempt and cast a negative pall over an otherwise exciting new prospect.


You Feel Good…

It is very important to dress for a date. This does not mean that if you are going to a park, you must wear a ball gown. However, attention and care can be showcased in casual wear and in a more formal look. Take a shower, brush your hair, make sure your clothes are clean and not creased. Unless you have a foot injury, wear proper shoes. This takes just a bit of time and clearly highlights your interest in your date and the chance to get to know her. It is disrespectful to arrive messy and disheveled and only tells your date that you don’t care and can’t be bothered.


Then You Do Good.

Sure, we are trying to get to know our dates on a deeper level and don’t want to be entirely focused on looks. This does not negate a need to do your best to look nice. Effort denotes enthusiasm and interest. Taking the time with your appearance tells your date that she matters. Be a mensch and dress to impress. Believe me, your date will notice.


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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.
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