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Dating Advice # 172: Online Dating Nightmare

May 9, 2009 | by Rosie Einhorn, L.C.S.W. and Sherry Zimmerman, J.D., M.Sc.

At their first meeting, she was already planning the wedding.

Dear Rosie & Sherry,

A few weeks ago I took a trip to meet a woman I had been corresponding with for six months via a Jewish dating website. Unfortunately the trip was not a success. In my mind I had developed an image of a perfect person that I had heard over the phone and read over Internet text conversations.

But upon meeting, I could not foresee her as my potential wife and the foundation of our home. Besides that I did not find her physically attractive.

To compound the problem, she had jumped many months into the future by already thinking that we where engaged and she was even planning our "wedding." I hadn't even met this person yet!

After our first date, I was ready to say goodbye. But since we had a weekend planned together, I decided not to break the news right away, so that the weekend wouldn't be ruined for her. On Saturday night I told her that unfortunately her thoughts of marriage would not become a reality.

Besides her desperation to get married, I found her lying about a previous broken engagement and exhibiting poor treatment of customer service personnel in stores and restaurants.

She took it very hard and asked me for a second chance but I refused. I ended my trip much earlier than expected and proceeded to return home then.

I don't know where to go from here. I corresponded with this woman for six months and now I have to start all over again. I'm very busy with school and work, and I don't have much time to go out and meet people. I got a really bad feeling and no longer want to continue online dating. (I live in a city with few regular dating opportunities.) Not only that, but I am very reluctant to travel long distance for a date.

I'm ready to start a long-term relationship, but I feel stuck in a hole and unable to come out. I fear that years will go by before I meet my soul mate.

Your advice?


Dear Jack,

We're sorry that your first on-line dating experience was not successful. It appears that you made some key mistakes that contributed to that. But don't get discouraged. Many people experience similar problems. The solution is to become educated how to identify and avoid the pitfalls in the future. Our article, "Maximizing Dot Com Dating" gives guidance about Internet dating that should be helpful to you in the future.

For now, we would like to focus on a few ideas for how you can make future on-line dating more successful:

(1) Arrange to meet earlier. Corresponding for six months over the Internet is way too long. You gave yourself too much time to develop an idealized image of what your e-pal was like. Even if she would have been an attractive woman, yet did not live up to the fantasy your mind had produced and then reinforced over several months, you would have been disappointed. In the future, don't keep up a virtual correspondence for so long -- try to meet within a month or two, if at all possible.

(2) Do advance research. Once two people get to the point of considering long distance travel to meet, we recommend checking references. Find out her name, city, the name of her rabbi, where she went to school, and whom she views as her mentors. Then, contact a number of these people, or have your own dating mentor (someone you confide in from time to time) help you make the contacts.

Checking out a potential dating partner is not a hunt for negative information. If you hear something negative, don't rush to pass judgment. You may be receiving incomplete or inaccurate information from someone who doesn't know the person or the situation well enough. That's why we recommend speaking to a few people, especially since no one person will likely be able to answer all your questions.

Here are some questions you could ask:

  • What are his/her family and siblings like?
  • What kind of relationship does s/he have with them?
  • Where is s/he headed in terms of spiritual growth?
  • What does s/he like to do in his spare time?
  • What are his/her friends like?
  • Have you ever seen him/her deal with challenges or crisis? How did s/he react?
  • Do you have any reservations about recommending him/her as a potential marriage partner?

In your case, a little advance research might have saved you a disappointing trip to a distant city. You would have learned about your e-pal's misrepresentations, the reasons behind her broken engagement (that in itself wouldn't be a problem, but you would have discovered that she did not tell the truth about it), and possibly other information that would have made you reconsider going to visit her.

(3) Don't ignore the red flags. This woman was planning your wedding before the two of you even met. We're always wary of anyone who decides that someone they have never met is "The One." Physical attraction and face-to-face compatibility are such important components of a relationship that people who ignore their importance may have difficulties with judgment and emotional maturity. Certainly, two people can develop an emotional connection over the Internet, but meeting face-to-face is obviously a prerequisite to moving forward.

Although you say that you are so busy with school and work, we would like you to make a firm commitment to set aside a certain number of hours per week for networking and dating, and spend the time making telephone calls, reading dating advice, talking to a mentor, and going out on dates.

In order to do this you will have to reassess your priorities. It seems that you are having difficulty doing this because dating seems a bit daunting. It is a lot easier to retreat to the "comfort" of a set routine of work, school, learning, and friends than rework your schedule and enter into the dating arena. If you stop for a minute and consider that unfortunately the dating scene is difficult for almost everyone, but is an inevitable stage you must go through in order to get married, it might give you incentive to make it your priority.

Keep your eye on the ball. The time you spend networking, checking people out, and dating may cut into your time… but it is the only way you are going to get married.

Wishing you success,

Rosie & Sherry


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