Photo Credit: Jewish Press

Dear Dating Coach,

I am dating a wonderful guy. We are both pretty new to dating, but connected right away. He is kind, and smart, and makes me laugh. Our dates feel both exciting and easy and I am very hopeful about where this is going. There is one thing though that I am embarrassed to discuss, but it really bothers me. He is the WORST dresser. He somehow is able to make black pants and a white shirt look like they don’t go together. His shirts are not nice and the styles he chooses are old fashioned and not flattering. His shoes are terrible, his socks are horrible, and I have not seen one item of clothing that has looked good. Please don’t think I’m shallow, but I hate his clothes and I feel awkward bringing it up – but I can’t get past it. Please tell me what to do.


Single Style


Dear Style,

We want to hang wallpaper in a small bathroom in our house. We have been talking about the wallpaper for months. The walls in the bathroom are covered in wallpaper samples hung with blue tape, highlighting our inability to commit. We have solicited opinions from everyone that walks into our home, pushing them to awkwardly detour to the bathroom. (The mailman thought this was especially strange.) Some samples have been declared “too stripey,” “too colorful,” “too colorless, “and my favorite – “too wallpapery.” The wallpaper pressure is real. If we make the wrong decision we will be stuck with the ugly, tasteless wallpaper forever. Or if that happens, we could just… hmm..take it off and change it?


An Outfit Can Be Put Away.

Congratulations on meeting someone that you can see a future with. This is a huge bracha and you feel really positive about where this is going. You are concerned about his style, or lack thereof. This bothers you and perhaps embarrasses you as you have noticed his many fashion infractions. You do not expect to marry someone who cares deeply about clothing, just someone who dresses with care. You are uncomfortable discussing this as it may diminish the connection you feel strongly about. Yet, he is poorly dressed and you are not a fan.

Kudos to you for seeing past an outfit on your dates. You knew immediately that here in fact the “clothes don’t make the man,” and you understand how precious his character and good middos are. That being said, you cannot imagine spending your life with someone who dresses this horribly, and you are not sure if it is your place to address it.


But Character Is Here To Stay.

The cool thing about clothes is that we get to change them every day. Unlike the Barbies living in my house who go for months wearing the same poorly chosen outfit, a real human has the power to change what they have worn, day in and day out. So, while it may be premature to let him know now that you don’t like how he dresses, it is definitely something you will be able to address as you form a closer bond, and certainly after you are married. Even after you are engaged you can begin to gift him with more stylish options (a nice tie or perhaps cufflinks) and you will have the ability to update his wardrobe more fully after you are married. Often someone who is “not into clothes” will be appreciative of the advice and style assistance from someone who cares. As long as you are kind and careful with his feelings, he will likely be open to the more updated clothing options you suggest. Clothes are not permanent; they are easily changeable. Instead focus on the respect and admiration you already feel for the person wearing them.


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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 [email protected] to schedule a phone session.