You came back from your first date seriously dissatisfied. He seemed distracted and “out of it.” Perhaps the conversation was awkward, the other person didn’t seem able to appreciate some things that are important to you. The conversation did not go well at all. Now, you are super-stressed by the whole experience, and you are wondering what you did to deserve this nightmare. You are barely able to contain your frustration when you tell the shadchan that you are going to do your best to forget this date ever happened. To your dismay, the shadchan suggests you go on a second date “just to be sure.” “Are you for real?” is your immediate thought. “Why would I put myself through this disaster again?” You would like to be left alone to lick your wounds, but instead you are being pressurized to try “one more time.” 

What next? Should you meet once more for a ‘second date’ or just tell the shadchan that this just isn’t going to work? You may be thinking: “Lousy date, next!” So, here are some thoughts to consider to help you gain perspective:

Why some first dates go wrong

There are many reasons why a first date may not go so well, meaning that it is quite possible that during a second date the conversation will flow better. Here are just a few examples:

• Many people are not themselves after a full day of work or school, and are not great conversationalists when they are tired.
• Plenty of  people become quite nervous on a first date, especially if they have little or no experience of dating. 
• Some people are simply shy, and take a while longer to open up. Many people find it difficult to talk about themselves to a “complete stranger.”
• Perhaps your date just heard some bad news or by something random that you said triggered a bad memory.
• Maybe he is self-conscious about a stain on his shirt, or she is uncomfortable about a hole in her tights.
• It could be the spot was too noisy, or she had been there on a previous date which made her feel awkward. 

With so many plausible reasons why a first date could go wrong, it is reasonable to imagine that a second date could turn out differently.

So should I go on a second date?

If the shadchan gives you a plausible reason why your date was not being themselves, or such like, it is wise to be open-minded about that. Not only would you want the same consideration, but there may well be quite a bit of truth to that. 

Obviously, every situation is unique. However, here are three simple principles that could help you decide:

• Unless you feel it is a truly definite no, it is best to give a shidduch a second chance.
• If both parties are not interested in pursuing it, it rarely makes sense to push it forward.
• It depends heavily on the reason for your hesitation: incompatibility versus poor dating experience – as will be explained below.

Lack of compatibility

If you discovered information that suggests you are incompatible with each other, then there is no real point in pursuing the shidduch. If, for example, it is clear that there are considerable gaps in your values, religiosity, life goals, and so on, you should direct your energies towards dating someone who could be your eventual marriage partner.

However, it is wise to consider that you may have got the wrong end of the stick. Misunderstandings happen all the time. Unless it is impossible to imagine a misunderstanding of that magnitude, it is worth going back to the shadchan with your perceptions and hear what they have to say. This is especially true when the perception you drew on the date markedly diverged from what you were told to expect.

“Just not feeling it”

You may regard yourself as intuitive enough to recognize whether or not the date has potential, and you may instinctively feel it is not a good fit. Perhaps his appearance doesn’t speak to you, maybe her dress left you cold, or it could be you felt that you just “didn’t click.” You may feel that is sufficient reason to move on. Perhaps. It might well be that it isn’t meant to happen, and you need to move on.

But perhaps not. A Shidduch is not about love at first sight. It is possible that upon further examination, his appearance is not the end of the world. She may show up to the second date dressed quite differently, and your reaction may be far more positive. Maybe once the nerves of the first date subside, you find that you are able to develop a connection. 

In many instances, when you are “just not feeling it,” it is best to talk it through with someone before totally dismissing the shidduch possibility. So many couples in long and happy marriages did not hit it off from the get-go. This is not some urban myth. Ask around, and you will find loads of stories like this. It is more important to have a fairytale ending than a fairytale beginning!

If, on other hand, you  

Understanding the Second Date

If you are going to go on a second date, you need to understand that in essence it is a do-over of the first date. You are going to put aside your previous conception based on your last experience, and come to the table ready for a new experience.

In other words, the aim of the second date in this situation is different to a regular second date. Here, your aim is to see if the dynamics have changed. That is why it makes sense to change things up a bit for the second date – such as different time of day or type of venue, or even consider changing dress style.

There could be a lot of nerves on a first date. Hopefully, on the second date, both can be more relaxed and get to know each other better. Remember, agreeing to a second date is not committing to a marriage; it is simply giving the shidduch a shot to unfold. 

“It isn’t nice to say no after the first date”

You don’t go on dates with someone to be nice or because you feel bad. That is not what a date is for, nor is it appropriate to mislead someone in this way. The only time you go on a date is if you sincerely believe that something positive may come out of it.

Dating puts both parties in a vulnerable state, and people might have painful experiences during the process. When a shidduch doesn’t work out, it can hurt. Everyone who engages in dating understands that.

Going on a second date in order to avoid hurting someone’s feelings is misguided. By going on a pointless date, you are not helping anyone. If you know there is no potential, why waste both of your time and emotions?  

True, it isn’t nice to say no after the first date, but it is never nice to say no after any date. You know what’s worse than saying no after the first date? Taking the other person on a date purely in the misguided belief that that makes you a nice person.

“I don’t want the shadchan to think I’m picky”

No, you do not have to go on a second date for the shadchan, and nor would any credible shadchan be asking you to give it another chance just for her sake – regardless of how much effort she or he put into the shidduch. 

If you really are concerned that the shadchan won’t propose another shidduch to you because you decline a second date you are sure will not work, this is obviously not the right shadchan for you.

If you’re the one who ‘made it awkward’

If you feel that you did not present yourself to the best of your ability, for any reason, it is important to let the shadchan know. They can then help the other side better understand the dynamics. Oftentimes, it is only on the second date that the potential for the shidduch is recognized.

If you Are Skeptical

Perhaps you are willing to be persuaded but remain rather unsure, so you are reluctant to go on a proper date if you realize after a few minutes that this is definitely not for you. That is a reasonable concern. If this is the case, you can meet for a shorter ‘coffee date’, where both parties understand that the commitment is to a shorter meeting. 

You might choose to do something lighter  – such as going to a museum – to see if you really want to share about yourself with this person, and if you are comfortable to do so. This date doesn’t have to involve an intense personal conversation. 

Ending a shidduch

Ending a shidduch can be a vulnerable time for both of you. How you end the relationship should be done with dignity and respect – for both of your sakes. Just be a mensch about it. The further along in the process the more sensitive the matter is. This is discussed more fully elsewhere.