Look for a coach who understands your community, listens carefully, explains how they work, and helps you make your own decisions. A first conversation should help you judge whether you feel comfortable being honest with them.
Looking for a dating coach can feel like another decision to get right. You may have a recommendation from a friend, a name from your shadchan, or several tabs open after searching online. Before comparing profiles, start with what you actually want help with.
Name the question you want to bring
You do not need a polished explanation. It might be: I keep saying no and I am not sure why. I want to start dating, but I keep putting it off. I am dating someone I like and do not know how to talk about something important.
That question gives the first conversation a purpose. Ask how the coach would approach it. You are listening for whether they understand what you mean, rather than whether they can give you an immediate answer.
Ask about both experience and training
Experience as a shadchan and training as a coach can each be valuable, but they describe different kinds of work. Ask what the person has done, what training they received, and which dating situations they work with. A clear explanation is more useful than a broad claim about helping everyone.
You can ask: What does a typical session look like? What would we work on if I am not currently dating? How do you help someone think through uncertainty without deciding for them?
Make sure they understand your version of frum life
Orthodox singles do not all have the same background, expectations or dating process. Your religious commitments, the home you hope to build, and the way your family is involved deserve to be understood individually.
Notice whether the coach asks about these things or assumes they already know. You should be able to explain what matters to you without feeling that you have to defend it or fit someone else's picture.
Pay attention to how the conversation feels
A helpful conversation can include questions you had not considered and feedback you do not immediately agree with. What matters is whether you feel heard and have room to respond honestly.
Ask yourself afterward: Could I say what I was really thinking? Did this person understand my concern? Did I feel invited to think, or pushed toward a particular decision? The choice of whether to continue dating someone remains yours.
Clarify privacy before sharing personal details
Ask who will know what you discuss, whether the coach ever speaks with parents or shadchanim, and how your permission would be handled. If a parent is paying for sessions, clarify what information, if any, they will receive. Ask about the written privacy terms and their limits rather than assuming that everyone means the same thing by private.
Understand the service and the cost
Confirm the session length, price, package terms, cancellation policy and any support between sessions. Also ask whether introductions or match searching are included. Some people offer both coaching and matchmaking; others keep them separate.
Be cautious about promises of a match or marriage by a particular date. A coaching arrangement can explain the help you will receive without promising an outcome no one can control.
Use an introductory call to decide whether to start
Bring one question and ask what working together would involve. You do not need to share your entire dating history or commit to a long package to make that first conversation useful.
At Matches by Adeena, new clients can begin with a free 10-minute discovery call. Adeena Halberstam works virtually with Orthodox Jewish men and women. She has 15+ years of experience as a volunteer shadchan and received a dating coaching certificate from Rabbi Dr. Yossi Ives. A single paid coaching session is 30 minutes and costs $125.
Her paid service is coaching. It does not include active match searching or guaranteed suggestions. The first call is a chance to explain what you need and see whether her approach feels right for you.
Want to ask Adeena about her approach?
Start with a free 10-minute discovery call. Bring the question that led you to look for support.
Book a Free Discovery Call