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How to Make Online Dating Effective
Dating Advice

How to Make Online Dating Effective

Help! I don’t know how to take things to the next level.


Dear Rosie and Sherry,

I'm a 30 year old man who has been using some online Jewish dating sites. I seem to be doing something wrong because after the initial contact where the girl says she's interested, I can't seem to get it to the next level. In fact I'm not even sure what the next level is.

Do I immediately ask to meet, or do I ask if she wants to talk on the phone or message? Should I immediately offer a reference so she knows I'm not John Wayne Gacy's nephew?

Part of me feels the next level is a phone conversation, since we are total strangers and I want her to feel comfortable enough to go on a date with me. However, when I go that route we either never connect on the phone, or she doesn't respond after asking if she wants to talk on the phone.

I'm really at a loss here. Please advise me on the proper protocol to follow and how to handle the situation. Any suggestions would be appreciated.


Rosie Einhorn, L.C.S.W. and Sherry Zimmerman, J.D., M.Sc.

Rosie and Sherry's Answer:

Hi Ike,

It seems to us that the reason your efforts to date online haven't gotten very far is that you're not making the right impression on women who contact you. Since you're not sure what to do next, you hesitate, and by the time you answer emails your prospective dates have lost interest.

We'll give you an overview of the online dating process and point out areas where you may be having difficulty so that your future online dating will be productive.

Your profile: Even though some women have responded favorably to your profile, you may still need to make some changes. You want to attract women whose worldview, lifestyle, and personal qualities are close to what you've been looking for, so that both of you are more likely to want to continue communicating beyond the initial exchange of emails. Your profile, including your photo (and any photos you post on Facebook and other social media) should be up-to-date and genuinely reflect who you are and what your lifestyle is like.

Write no more than three short paragraphs for the "essay" that accompanies your profile. Your goal is to describe the qualities that make you a unique person and a good candidate for marriage-oriented dating. You want a profile that is concise, easy to read, and gives enough information to pique another person's interest.

Talk about what you're doing with your life, what values are important to you, and where you see your life going over the next several years. Describe three or four of your strongest positive character traits, and talk about the things you like to do. Briefly mention three or four of the qualities you're looking for in a future spouse. You can use humor, but avoid sarcasm, and don't start explaining your philosophy of life. Ask a couple of good friends who can be honest with you to screen your profile and photos and give their honest opinions about their accuracy and appeal.

Responding to emails: It sounds like you’re taking too long to respond to emails from women who are interested in you. Could it be that you’re hesitating because you think that replying means you're making a commitment to go on a date?

Relax. At this point the two of you are simply changing a little more information to see if you're in the ballpark for each other. If her email sounds interesting, write back to her within a day. If you delay too much longer, she may think you're not really serious about dating, are not really sure of yourself, are not really sure about her, or aren't considerate.

Answer her questions and ask for any more information you'll need to decide if you'd like to take the next step, which is a telephone call. Don't go on and on about yourself; strike a balance between describing yourself and showing you are interested in her. You can add a little humor, but at the same time be yourself and don't come off as trying too hard. Remember that your answers should not give personal details such as your full name, address, employer, and home phone number.

The Phone Call: After exchanging two or three emails, you should have the information you need to decide if you want to talk on the phone. There are many reasons why it's not wise to have a lengthy email correspondence:

Some people write very well but have trouble communicating on the telephone or in person.

Online chemistry can be very different than the chemistry that develops during a phone call or a face-to-face meeting.

Some people will never move past emails or telephone calls because they use dating sites for entertainment or fantasy and aren't serious about dating, or are too shy to meet.

After many back-and-forth emails, we may build an image of what the other person is like and have trouble reconciling this with who they are on the telephone or in person. It sounds like you may have dropped the ball here as well by waiting too long to suggest speaking on the phone, by limiting your availability for calls, or by waiting too long to make the call after you exchange telephone numbers. In the future, when you exchange cellphone (never home phone) numbers, arrange a time to make that first call and follow through. If you feel awkward about the conversation, plan out how you'll open a few different topics. Try linking some of the topics to something she said about herself - a hobby, a book she read, an event she attended. Think of the call as a chance to hear how each other sounds, to get a glimpse of your personalities, and to find out any other information you'd like to know to decide if you'd like to ask her out.

Remember that your goal is a real date, not a series of "phone dates."

The First Date: Even though some Jewish online dating services screen their participants, you can't take that for granted. Be safe - arrange to meet in a public place, preferably a cafe or coffee shop, so that you can limit the first date to 60 – 90 minutes and you can focus on talking instead of eating a full meal. Until you actually meet, it's still too early to exchange personal details. Make sure a friend knows where you'll be and have an exit strategy in case the date turns out to be a bad experience.

Think of the first date is an ice-breaker. Be prepared for the fact that each of you will look a little different than your photos and may not be the same as you are on the phone. Check your expectations; you're just meeting someone you seem to have things in common with, and will have a chance to see what she's like in person.

On the date, if you're comfortable with her personality and would like to see her again, you can tell her so and ask for last names and references. You can explain that you'll speak with her references over the next few days and get back to her. (She'll probably want to check you out as well.) Don't drop the ball here, either; make the calls as soon as possible, and then call to arrange a second date or to let her know you don't think you're right for each other. Don't leave her hanging.

Contact Potential Dates on Your Own: You haven't mentioned your own efforts to review profiles and contact women who seem interesting to you. Are you doing that as well? Don't just wait for women to contact you; be proactive. We hope that you'll soon change your Internet dating experience for the better.

Good luck,
Sherry and Rosie


September 10, 2016

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Visitor Comments: 5

(5) Anonymous, March 17, 2017 2:26 PM

Very interesting question and answer. Dating in general is not easy, be it online or offline. They both have their advantages and disadvantages. I have signed up to loads of them and some work and some clearly don't but the main thing here is to stay positive, make sure your profile is funny/witty, upload good quality photos to your profile and when you send a message, make an effort rather than "Hi, How are you?".

I am currently single (again!) and have signed up to a few dating sites in the UK and found to be doing well for me. Even-though I haven't found anyone yet, I have certainly met a few friends/very interesting people.

Stay positive people and don't forget, there's someone out there for everyone :-)

(4) Bobby5000, September 29, 2016 12:37 PM

social skills

Please accept this as a well-intended suggestion and you may be a very nice person. You need to work on your social skills and what is acceptable and appropriate in various contexts.

You wrote, "Should I immediately offer a reference so she knows I'm not John Wayne Gacy's nephew? References to a murderer,, here someone who did awful things to children, are inappropriate, for initial contacts. You may also want to check your online presence. Learning about small-talk and customs in various contexts.

A good start is Dale Carnegie's Book, How to Win Friends and Influence People. Asking about the other person's interests is a good start. Be a good listener. A woman friend complains that men launch into long-winded discussions of their accomplishment and seem to have little interest in their interests. On dates, make sure you have selected nice, higher-end clothes.

(3) Gary, September 16, 2016 3:06 AM

Maybe this will help?

Try asking the One who introduced Adam's wife to him…If anyone knows the best girl for you to marry just might be the One who instituted marriage in the first place…Don't ya think?

(2) Y W, September 15, 2016 1:44 PM

Be optimistic but cautious

Run a background check on people whom you do not know. My son married a felon he met on jdate, with disastrous results.

(1) Anonymous, September 15, 2016 1:31 PM

No luck either

My experience is that via a "Jewish" dating site the only women whom have made first contact were either obvious cat-fishing attempts and/or non-Jewish women not willing to convert.

All attempts at messaging or flirting on my part usually go unanswered or rejected. I've tried having a professional write my profile, but the one hit I got thought I wasn't being honest enough when they started asking me questions. So I wrote a new profile myself which is probably overly honest and hasn't had any success.

I've even tried matchmakers, but only came out with money lost and nothing to show for it.

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