Photo Credit: Jewish Press

Dear Dating Coach,

I am a “Bais Yaakov type” who has been having a harder time dating than I expected. I try to keep busy by going to work every day at a job I really enjoy, exercising in the evenings, having meals with my two roommates, and running errands and taking care of miscellaneous chores on Sunday. I recently noticed that I may be developing feelings for a coworker of mine. He is much older than me, not nearly as religious, and not what I expected, but I still find myself interested in him. Should I pursue this since I’m obviously interested?




Dear Unexpected,

I love Disney World. The rides, the lights, and the atmosphere all get me every time. I always seem to come back to the classic rides that never disappoint. That dirty foot in Pirates of the Caribbean, the vomit-inducing tea cups, and the race track that makes you second-guess your driving skills. Every time I ride “It’s a Small World,” though, I am struck by the beautiful displays and the similarities that unite us. I often marvel, however, as we float through, at the word choice, because regardless, it is in fact quite a “big” world after all.


Spread Your Wings…

Thank you for reaching out. Dating is hard. It’s harder when it takes longer than you ever envisioned. You feel like you have been using your time productively with work filling the bulk of your waking hours. You recently noticed feelings you may have for a coworker who does not fit the criteria in any way that you hoped for or expected. You wonder if this matters enough to not pursue this possibility. You feel conflicted as you struggle simultaneously with the appeal.


…And Fly.

I hear you.

Listen carefully. You are trying so hard, but in this process, your shrinking world was reduced to a tiny little box wrapped in a tiny little bow on a tiny little island. When our circles and our connections become so limited, we naturally do our best to connect with the possibilities we do have. But there is more. There are more. You need to explore more.

Please don’t think I am minimizing what you feel, but you must immediately expand your circle, your horizons, and your world. There are appropriate, suitable options for you in our frum dating world. By closing yourself off in the small world you find yourself in, you are forgoing the chance to have everything you ever hoped for. Attend community events, celebrations, and family gatherings. Go out for meals, join single events, volunteer, travel, and give yourself the gift of choice. Trust me, you are worth it after all.


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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.