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My Dating Dilemma: Should I Cut My Losses?

My Dating Dilemma: Should I Cut My Losses?

We have different backgrounds and lack depth in our relationship? Should I take things further? How?


Dear Aleeza,

I’ve been dating someone for about three months. On our latest date, I felt disconnected and withdrawn from her on the date. In general, we have a decent connection, but today was different. The date wasn’t amazing, but it also wasn’t terrible. Still, I’m afraid of continuing because I’m starting to feel distance between us. I'm now starting to doubt the future of this relationship and question whether we are compatible.

There are two key points that lead me to this conclusion:

  1. We have different backgrounds. I feel like we can't connect on an emotional level because we hang out in different crowds. How important is it that we have a similar circle of friends?

  2. I don't feel like there is depth to our relationship. We go out, have a nice time, talk on the phone, send texts, etc. We haven't had an intentional discussion about our long-term goals, what we need vs. want in a spouse, what our strengths and weaknesses are, or our hopes and dreams for the future.

I asked her if she would be open to the next date being a schmooze date instead of an activity date. She agreed to that. I’m all set to have a mindful discussion. Any pointers on how to have this discussion from a place of curiosity and interest instead of fear and judgment?

Mr. Doubtful It Will Work

Aleeza Ben Shalom

Aleeza's Answer

Dear Doubtful,

A client of mine once told me a joke: Sincerity is everything. If you can fake that, you've got it made!

But seriously, the best way to approach your upcoming conversation would be to come from a place of sincerity instead of a place of fear. You mentioned several key points that I want to address.

1. Disconnection and distance. Couples are expected to have times of connection and time of disconnection. You mentioned that you generally feel like you have a decent connection, but recently you experienced a feeling of distance. You should expect some ebb and flow to happen in all relationships. If this was your only concern, I would tell you to dismiss it at this point and encourage you to continue dating. As long as you’re connected more often than not, I don’t see this as a serious problem. As a guideline, I like to see couples connected around 80% of the time and allow for healthy space 20% of the time.

2. Fear of continuing. Fear of continuing in a relationship because of the uncertainty of the future is very common. Some singles will end things after just one or two dates for this reason. I’m glad you allowed yourself to develop the relationship further and see what there truly is between you two. While fear is a normal, healthy response, it is also one which we should combat with time. Only time will reveal what is truly there in a relationship. Perhaps your fears are founded, and it’s time to end the relationship. Or perhaps in time you will see that the distance between you two is normal and a healthy way of maintaining your relationship. Take note of how often you’re feeling connected and how often you’re feeling disconnected. In particular, try to note if anything happened to create those feelings. The more information you have about your relationship, the more fairly and honestly you can evaluate whether to continue or break up.

3. Different backgrounds. Great question! Not everyone gets to marry the girl next door. Not everyone wants to! In general, I believe that it makes a relationship easier if you have more things in common. Having different backgrounds or friends can sometimes work. On a practical level, are there any couples you could envision the two of you spending time with and both enjoying? Making friends with another couple is often nearly as challenging as finding your soul mate. What I hear you asking, though, is a deeper question. I hear you asking whether your choice in friends indicates value differences rather than preferences. You may be onto something.

Take a look at what she values in her friends. Why does she choose those friends? Then ask yourself why you choose your friends. Some people choose friends to relax and hang out with. Some prefer people with whom they can connect on a deeper level. Others choose friends by sense of humor and hobbies. On your next date, try to identify a few key values related to how she chooses friends, and share with her how and why you choose the friends you do. I think you’ll find it more helpful to see if your values match up than if your specific circles of friends do.

4. Sharing hopes and dreams. This is an interesting topic. While these things do matter, your dreams and goals are not reality; they are simply thoughts. Keep in mind that while you want to align yourself with someone who will be right for your future, it’s also important to align yourself with someone who is right for you now. A good way to elicit what you want to know about someone is to first provide that information to them. Lead the way by telling her something about your hopes and dreams for the future, and then ask her how she sees things. Be careful not to share only the things that you think you feel the same way about. It’s fine to have a different vision or goal for the future. The more honest, open, vulnerable and real you are with your date, the more you two can evaluate whether or not this is a good match.

I believe you are asking sincere questions; the answers will require you to spend more time in your current relationship in order to come to an authentic conclusion. I’d much rather you date a little longer to figure it all out than cut things off too soon out of fear. Don’t be afraid that you are leading someone on when you aren’t 100% into them. Date with intention and sincerity and you won’t be leading anyone on. Be curious about your future together and ask more questions to discover your true level of interest.

When you bring the relationship to a deeper level you will be able to evaluate your real concerns and then either move things forward or end the relationship--without ever having to look back in doubt.

November 21, 2015

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Visitor Comments: 4

(4) Bobby5000, November 30, 2015 11:17 PM

bad vibes

If you are getting bad vibes, you need to DECREASE your relationship rather than seek to deepen it. The last thing you need is to push her into a marriage where you are second best, she doesn't feel real affection, gets married because that's the thing to do, and finally sees the man she really likes when she is 34 with 2 kids. That's not good for anyone.

(3) Devorah, November 28, 2015 10:56 PM


I am the same person I have always been. The core of me has never changed. My preferences have changed as have priorities which tends to be complimentary to any situation I am in. I have had relationships work well for years. Mutual respect even admiration. Our differences have at times been on opposite ends yet knowing one another which over time grew in depth and perception, we overcame these obstacles. Of course, these are friends I have known since childhood. Though we have known one another forever they still manage at times to pull the rug out from under me. As I do them every so many years. We went totally different directions at times but in the end our reflections on these experiences brought us closer. This is when trust is relevant . Give people the room to grow. It enriches your relationship. If you share your humanity with others who hold the same ideal, you will not fail. This is something you cannot fake nor should you. Never be something your not. You will attract the wrong people that way.The truly tough part is to find those who see you as you see yourself.

(2) Anonymous, November 27, 2015 5:46 AM

Good points, BUT

I usually don't bother to conceal my name, because I don't feel I have anything to hide, but this one affects others.
"...align yourself with someone who is right for you now." -- Essential, BUT: I am divorced. One of the reasons is because I was not the same person at 35 or 45 as I was at 25, when we got married. Yes, future ideas are just thoughts, but it is certainly worthwhile to check to see that she HAS some thoughts, and that they resemble yours. Otherwise, you could find yourself in a relationship "down the road" that wasn't what you had planned in the here and now.
Serious topics: I am hoping that your relationship is one that the two of you entered with the "goal" of marriage in mind. The absolute least that can be said about meeting as a "shidduch" or through a shadchan, is that you know where you are heading.
I recently sat my ladyfriend down and prefaced my remarks with, "I like you a lot, and I very much enjoy hanging out together with you." Then I went on: "But, do you WANT to get/be married? Do you understand that we entered into this with a fixed goal that cannot be ignored for six months or a year?"
You might not need to be THAT serious (like I wrote, we both had this understanding prior to my speech), but you definitely need to be on the same page.
That's just my opinion, but it is based on personal experience and long-term reasoned out feeling and thought.

(1) Abe Shainberg, November 26, 2015 5:13 PM

Keep going and learn.

If there is potential, give the relationship a chance. make sure you know what your red flags are.

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