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Dating Maze #291 - Third Try?
Dating Advice 291

Dating Maze #291 - Third Try?

She broke up with him twice. Is it time to give up?


Dear Rosie & Sherry,

I dated a young woman for a month and I felt it was going very well when she suddenly ended it without giving a reason. I got up the nerve to call her to inquire why she had ended it, and she said she wanted to continue dating me again, no reason given.

We went out again within a matter of days, got along well and never discussed why she had ended it. It became clear that she was under some kind of pressure to know whether I was "The One" soon into the courtship. Two weeks after we started dating again, she told me that she couldn't continue as she didn't feel it was progressing. She was unable to elaborate or offer any reason to the friend who had set us up, and seemed very confused, saying that I had all the qualities she was looking for. I decided not to pursue it any further in spite of my feelings.

Is her behavior normal? Is it normal that I should still be thinking about her a few months later? Should I wait a year and try with her again? And do I need to get over this before I decide to date other women?


Dear Mike,

It sounds to us that you were dating a young woman who could benefit from guidance about how relationships develop and what dating expectations are realistic and unrealistic. At the same time that she was second-guessing herself because things weren't developing as quickly as she felt it should, you felt there was real potential and you were developing feelings for her.

It's very common for daters to become "invested" in their courtship at different rates, and it is often the case that the man feels an emotional attachment to the woman before she feels the same. It's unfortunate that this young woman didn't stay in the courtship long enough to see how things developed. If she was less confused or had a knowledgeable dating mentor, your courtship may have continued to progress. But it is also possible that you would have discovered that you weren't right for each other.

It isn't unusual for you to be thinking about this woman even a few months after the break-up. Clearly, she "got to you." Sometimes it takes several months to get over someone whom you really felt connected to. But we also think that one of the reasons that it's hard for you to stop thinking about her is that you believe that the two of you really had a chance. Therefore you can't accept the idea of the break up because of this and you are still hoping that in time, she'll learn a little bit more about herself and about dating and you can try again.


She needs to address the reason she broke up in the first place.


It sometimes does happen that couples who stopped dating for one reason or another go out again, and the second time their courtship succeeds. But that only happens if they address the reason they broke up in the first place. The woman you were seeing would need to address the reason she ended things, and she would need to determine that it's not an issue any more. A dating mentor might be able to help if she broke up because she didn't really know what she wanted, or had unrealistic expectations. But if she decided not to continue because there really was an issue that she was simply unwilling to share with you, she'd have to resolve that issue before she could agree to go out with you again.

For now, however, you need to move forward. There's no benefit to putting your social life on hold for a year in the hope that during this time the young woman you dated will gain more clarity about herself so that the two of you can try again. A year from now, each of you may have grown in different directions and may no longer be well-suited to each other. If you are really determined to try again with this young woman, then explore that possibility now. We would suggest calling the mutual friend who first set you up to say that you are still interested in this young woman, believe she broke things off because she was pressured to know if you were "the one" far too early, hope that in time she has been able to get some good advice about dating, and wonder if she can be approached about going out again.

If you get a "no" answer, then it is best for you to tell yourself, "Even though I have strong feelings for this woman, I'm going to put it behind me for good."

This closure is very important to your healing process. Once you are able to acknowledge that your courtship cannot be resurrected, you will be able to let that hope go. You'll still feel disappointed that things didn't work out, but that will diminish with time. Many people have experienced similar disappointments -- things didn't work out with someone they liked a great deal or really felt connected to, and it takes time to mourn this loss.

But there actually is something beneficial about having this experience. It means that you felt very connected to another person, and it lets you know that you can relate to someone else this way, and it gives you encouragement that you will be able to connect to someone who is truly right for you.

Once you can acknowledge that, you can start dating again. In the beginning, you may have to remind yourself that your former date wasn't The One, tell yourself that her memory can't accompany you on your dates, and tell yourself not to compare your feelings or your reaction to the new person you are dating to how you felt with her. In time, you'll be able to date without having to give yourself these reminders.

We wish you success in navigating the dating maze.

Rosie & Sherry

September 6, 2009

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Visitor Comments: 10

(10) Anonymous, September 25, 2009 4:14 AM

Never Give Up

I was young and immature when I first went out with my now- husband. I happened to have broken up with him numerous times because of fear/ anxiety/ unclarity. Lucky for me, he was the persistent type who wouldn't let me go. Thank G-d today we are happily married with children for 10 yrs! SO if you feel it's right, push along.

(9) Anonymous, September 17, 2009 10:12 PM

What about chemistry?

I completely agree with the woman that wrote 'what about chemistry?' I almost settled for the wrong man because he had everything else I wanted! it was interesting to see that this woman actually married the man. I always wondered if I could MAKE IT WORK. But if it doesn't work a woman will most likely break it off or settle, I suggest that you get over it and find someone that loves you for who you are! Best of luck to us all!

(8) Eric, September 14, 2009 10:23 AM

felt same way about woman I dated many months ago

I dated a woman from Toronto many months ago. It seems like I felt the same way as this guy, well sort of. I'd say that this woman was who I'd consider to be my first girlfriend later in life because I knew the colour of her eyes, green (that she called hazel). It wasn't an on-again, off-again courtship but was emotionally disconnected. I worshipped this woman and it seemed like I was in love with her after six months. It was infatuation and obsessive admiration. I became jealous that she gave her time to others in her city while I was in Halifax. After a while, I appeared posessive because I wanted more time with her but didn't find an effective way to express it. When I dumped her, playing the typical friendship card, she didn't take it well, and called me cheap through the matchmaking team at Saw You At Sinai. I was never cheap in that I gave part of my soul to her through personal photographs and videos I made. These were carefully selected and put on a CD-ROM as one gift that I gave to her when we dated. She was hurt and I was hurt even more when we broke up because I thought there was hope that we'd stay in touch as friends. I sent her Facebook messages many months ago that she just read a few weeks ago. These messages were probably read by her and she decided to remove her profile from Facebook. Maybe these were too much for her. I have a feeling that we may meet again one day. Until then, the feelings of emptiness without her have subsided. I think about her from time to time but only in that I learned how to grow as a person from having met her. I hope that she learned the same thing.

(7) Aron, September 12, 2009 3:31 AM

Anonymous (4) has got it right--Attraction is main thing.

Contrary to what many guys believe, whether a woman is attracted to you is NOT the result of anything you SAY or DO. It has to do with just 1 thing--what you ARE. Just be yourself. Because she's either attracted to you or she's not, REGARDLESS of how you try to appeal to her. Other than normal hygiene & dress & manner, don't ever TRY to win her over. The fact that you even took up with this gal again, after already being dumped once, perhaps conveyed a sense of desperation which ultimately took over & killed your appeal for her. Next time you meet someone who attracts you, DON'T TRY to impress her. Joke, flirt (if it feels natural ), have a good time, be silly as you wish (or not)...& above all, take it easy. Got it? Better luck next time.

(6) FEIVEL PELTZ, September 10, 2009 1:19 AM

Excellent advice

You guys really hit the "nail on the thumb." Never read your column before, but I won't miss one now.

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