woman thinking

Why Do I Regret Saying “No” to People I Dated?

Dear Dr. Chani,

I really need your help. I have been dating for quite a while, and I noticed a pattern that I have. I tend to regret my decisions. It is interesting because it is not that I am indecisive. I usually have an easy time coming to a decision about whether to continue or not. Sometimes it takes me two dates, sometimes several more, and sometimes the guy decides for me! When I make a decision about whether to continue dating someone or not, I think about how our conversations were and if we seem like we might make a good match. If we do, then I keep on going. If we do not seem like that, then I tend to end it. I usually feel like I made a pretty good decision.

What kills me is the second-guessing that I have afterward. Later on – it could be months (and now years already) – if I see a former date that I said “no” to, I drive myself crazy thinking if my “no” made sense. I eat myself up trying to think if I made a premature decision. There are two things that really make me go off the handle in second-guessing myself. The first thing is if I see him in a relationship with someone else. Then I kick myself and wonder if I was stupid for letting him go. The second is if I am in a relationship that is going well. If I see a guy I had previously dated while I am dating someone else, I compare them and I ask myself if I should have kept going with the previous guy instead of being on my way to becoming committed to the guy I am currently dating.

I am now going through torture since both happened. I have gone out for a while with a really great guy. We seem to have a connection and a mutual understanding. However, we were at a Friday night meal and a guy I had gone out with was there – with his girlfriend. I only went out with him a few times, but my head is going crazy. I am very happy to be going out with my boyfriend. So far things seem really great. But when I saw this girl smiling and kidding around with her boyfriend, I started second-guessing myself. Should I really be with the current guy? Was I stupid for saying no to that other guy? Maybe I did not put in enough effort, and it could have worked with him.

There is one more thing. I notice that the guy I had gone out with dresses in a cooler way than the guy I am going out with now. It does not bother me so much, and I can certainly potentially make it work with my current boyfriend. But I still wonder what could have been. I am beating myself up.

I went for counseling over this. The therapist told me that I am very self-critical, so I will always second guess myself. I should just “welcome the thoughts” and move on in my relationship. I would – but I can’t! What should I do? Please help me.



Dear Suffering,

It is not easy to make decisions in dating. Every person you date is an opportunity to get to know someone. Every relationship can potentially lead to you marrying your life partner. Although you find that your initial decisions to end relationships feel balanced, logical, and comfortable at the time you make them, it makes sense that you second guess your decisions when you are not entirely happy with your experiences in the aftermath of your decisions. It sounds like you tend to regret saying “no” to people you previously dated specifically when you encounter someone or something that reminds you of your original decision.

You feel you are competent at making decisions in the moment, but not afterward. This can be because whenever you see a representative of the decision in front of you, you feel like you are being faced with making the decision again. Your brain sees the choice in front of you and it goes through the calculations you had made, all over again. The problem is that it is hard to recall all the reasons you originally made a decision. So when you are faced with it again, you are also faced with analyzing your decision again. Yet, this time you do not have the full facts in your mind as easily accessible as when you had made the decision originally. You may actually have a negativity bias when evaluating a person you are currently dating but have a positivity bias when evaluating someone you previously dated. This is because you tend to focus on the positive when you cannot have something. As they say, “the grass is always greener on the other side.” 

So how can you approach your dating decisions with a balanced perspective? One of the key factors in making a decision with clarity and confidence is to use your thoughts to guide you. Based on your description, it sounds like you rely more on your emotions, your feeling of connection, and your impressions of your conversations. While these are important aspects to consider when deciding whether or not to continue dating someone, they are not enough of a basis for making a balanced decision. Since these are more based on feelings than facts, they are more amorphous and fleeting. This is why when you try to reconstruct your decision at a later point or explain it to someone else, you might have a hard time. Feelings are important and very significant, but they are not quantifiable. 

A better way to come to your dating decisions with clarity so that you are less likely to regret your decision is to create a tangible list of qualities you are looking for. Then you can use your top five most important qualities to assess the extent to which the person you are dating has those qualities. If he has the qualities or seems to have the potential to have those qualities but you have not been able to observe them yet, continue to date him and invest in the relationship. However, if he does not have those qualities and you are uninterested, you can break up with him with clarity and confidence. If you feel you are not sure what to include on your list, seek guidance from someone who can help you.

Let’s also address a quality that bothers you about your current relationship. You mentioned that your current boyfriend is not such a cool dresser. You seem to easily dismiss that by saying you could “make it work.”  Sometimes, when something bothers you and you try to ignore it or minimize it, the problem snowballs, The issue lingers in your mind, even though you keep telling yourself that it does not matter. This makes it more difficult to “get over”. Instead, your disappointment festers. Then, when you are faced with someone else who dresses in a cooler way, it awakens the feelings you have been repressing about how your boyfriend dresses. Your mind wonders what it would be like to be in a relationship with someone whose taste in clothing you respect. Even if you were not inclined to regret your past decision, seeing a person who you previously dated and dresses better than your current boyfriend magnifies your unresolved disappointment about the way your current boyfriend dresses.

If you are bothered that your current boyfriend is not such a cool dresser, acknowledge that this bothers you to some extent. It can be more truthful – and beneficial to your relationship –  to tell yourself that he has many positive points and some negative points. One of the negative points is that he is not such a cool dresser. Despite that, you are drawn to him and his positive traits. Tell yourself this and do not try to ignore it.  As you acknowledge it and accept it as a fact, you might find that you do not mind it so much. Be in touch with what is bothering you and do not hide it. The more you explain to yourself why it bothers you, and explore ways you might resolve it, the more you can overcome it. This can help you get more clarity and appreciate your relationship with your current boyfriend.

Developing a clear and concrete understanding of what matters to you will help you to identify the person who is right for you and appreciate him. I hope this helps you break free of your pattern of regret and paves the path for your commitment to a person who you appreciate and who appreciates you!

Wishing you much success,