The Number Of Dates You Need To Go On Before Deciding If A Relationship Will Work

Just because you're nervous before a first date, doesn't mean the relationship is doomed.

Last updated on Mar 30, 2023

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By Dr. Seth Meyers

Let’s get right to it: After two or three dates, you should honestly know if the person you’ve met is someone you should keep dating

Too often, a mistake men and women make early in dating is overthinking things. By date two or three, you won’t know if this person could be your lifelong partner. But after two or three dates, you will know if this is a person you inherently feel comfortable with. By two or three dates, you will know whether this person is someone you have a natural fit with, and that natural fit is the must-have foundation of any good, lasting relationship.


Many times, a man or woman will go on a date and feel understandably nervous because they are meeting someone new. Everyone’s heads are filled with questions as they sit at dinner or walk down the street together, wondering a million things. Does the other person seem truly interested? What is their body language showing? Does it seem like they feel attracted to me? How attracted do I feel to them? These are normal questions and thoughts everyone has about dating.

Here is the number of dates you need to go on before deciding if a relationship will work: three.

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But sometimes people overlook one of the most basic factors in dating: How comfortable do I actually feel with this person?

Why don’t I feel comfortable with some people's dates?

There are countless factors that can make you feel uncomfortable with someone. Perhaps your senses of humor don’t align; perhaps your date is a guarded, hard-to-connect-with person; perhaps your date doesn’t know how to connect easily with others. It is imperative that you think about this issue — how natural and comfortable you feel — from the very start of any relationship.

If by date number three there is still discomfort in the air, listen to this instinct as if it were an emergency alert system notifying you of a disaster. (Sounds a little dramatic, but do you know how many relationships end in disaster?)


If, after two or three dates, you still don’t feel comfortable or at ease with this person, my years of experience tell me that you are working too hard to make something fit that perhaps isn’t supposed to fit.

Did most long-term couples feel comfortable when they think back to their first date?

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If you poll a host of couples who have lasted a long time (say, more than ten years), most of them will tell you that they felt comfortable and at ease from the beginning. Of course, we have all heard examples of long-term couples where one or both members share a story where they say they didn’t at first like that person, or they thought he or she was rude, arrogant, or even boring. Trust me when I say that these couples are the exception and not the rule.


Keep your dating principles simple and clear, and the most fundamental one you should follow in dating is to focus on finding someone you almost instantly feel natural with and comfortable with.

Some men and women in long-term relationships tell others that they knew from the start they would end up being with that person for life. What they are really saying is — wait for it — they felt totally comfortable and at ease with that person from the beginning. This, as they say, is “the stuff that dreams are made of.”

I hear so many people say they hate dating, and as a therapist who specializes in relationships, you can imagine that this cynicism breaks my heart a little each time! But people who hate dating aren’t finding people they instantly feel comfortable and at ease with. (If they were, they wouldn’t hate dating.)

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You can’t force yourself to feel at ease with someone — no matter how much you want it to work.

Going forward in your dating life, mind this simple rule: If you don’t feel at ease with your date by the end of your third date, don’t push yourself to feel comfortable when the dynamic simply isn’t there. People sometimes hang on too long to try to make it fit because the other person has some characteristics that are extremely appealing. They may be off-the-charts attractive, very successful in work, or have an overall lifestyle that seems exciting and fun.

Reality check: If it doesn’t feel right, it won’t be right. While dating is inevitably unpredictable, dating doesn’t have to be — and shouldn’t be — unpleasant.


If your dating experiences are resulting in a pattern where you feel frustrated and unsatisfied, give yourself a chance for something better by facing the cold, hard truth. You need to look at what decisions you’re making in your date selection process that is making you feel worse, not better. The consolation, of course, is that there is nothing stopping you from change!

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Dr. Seth Meyers is a licensed clinical psychologist, author, and TV guest expert. He treats a wide range of issues and disorders and specializes in relationships, parenting, and addiction. He is the author of Dr. Seth's Love Prescription: Overcome Relationship Repetition Syndrome and Find the Love You Deserve.