Dating 101: Should You Give That Awkward Guy Another Chance?

Recently, I’ve been hearing more and more wild dating stories, and they all seem to end the same way: in the end, the guy got married.

And I find myself wondering how it’s possible that such an insensitive, unrefined, or simply odd guy managed to make it to the chuppah.

The simple answer is that Hashem takes care of all His creations, and for every pot, there is a lid. But there’s also another answer, one that has a lot to do with human effort.

Someone gave him a chance.

Someone looked beyond the awkward comment, beyond the insensitivity, and decided there was something more there.

Should You Give It Another Try?

And what about you? What would you do in that situation? Would you give him another chance? Would you agree to meet again?

When is it wise to try again, and when is it a waste of time and energy?

In the vast majority of cases, it’s really not advisable to cut things off after the first meeting.

At a first date, you’ve barely begun to get to know the person, even if it feels like you already understand him completely. You still haven’t encountered the different layers of his personality, even if he talked nonstop for three hours. First impressions matter, but they are often shaped by stress, nervousness, awkwardness, or discomfort on one side or the other.

That’s why it’s usually wise to hang in there, even if something felt a bit off, and give it at least one more try.

When Not to Continue

Always?

Almost always.

And when not?

If you arrive at a meeting and he casually mentions girlfriends he’s murdered.

Come on.

Or if he excitedly announces that his lifelong dream of permanently moving to Egypt is finally coming true, or that he intends to convert to Christianity. Aside from extreme or clearly incompatible situations like these, it’s worth trying to push past the initial discomfort and give him another chance. After all, you’d want to be treated the same way.

Appearance, Discomfort, and Knowing When to Stop

And what about appearance?

Give it a few dates before deciding.

And if you did give him a chance and it still didn’t work?

If you genuinely tried and nothing improved, then it’s okay to end the connection. If you reach a clear conclusion that it’s not right for you, make an effort to end things as soon as possible and don’t drag it out because of discomfort.

He would rather feel disappointed now than continue building hopes when your heart isn’t in it. The longer things go on, the more expectations he’ll develop, and the deeper the hurt will be when it ends. Your discomfort won’t fade with time; it will only grow.

As time passes, communication deepens, closeness develops, and in some cases, people even find themselves married simply because they didn’t have the courage to stop earlier. Yes, it happens.

So even though it’s not easy, gather the courage to take that difficult step. In the long run, it will bring both you and him closer to where you truly belong: under the chuppah.

Nechama Bitkover is the head of the Depth of Connection institute and a relationship coach.