Isaac was a textbook nice guy. He easily put himself second and was a consummate gentleman. Sadly, his dating was not a success, as successive women felt that for all his niceness, they didn’t feel comfortable continuing the relationship. It was challenging for Isaac to figure out what was going on, because the women he had met found it easy to say nice things about him. Yet, they didn’t want to continue dating him.
Slowly and painstakingly, however, it became clearer that was behaving in ways that made the women he was dating feel uneasy. Isaac was extremely self-deprecating; he would constantly put himself down. It would be especially pronounced if his date made the ‘mistake’ of complimenting him. He would speak negatively about his appearance, about his intelligence, even about his desirability: “I wonder what people see in me.”
Isaac was also a classic people-pleaser. It was obvious to those whom he was dating that his opinions or preferences were entirely calibrated to match the person he was with. He didn’t seem to hold a single position of his own. Whether it was where to go on a date, or a political issue – he came across as if his only priority was to not cause offense. Several of his dates urged him to just be himself. But, – but that was him being himself!
Isaac seemed unable to resist injecting self-doubt into almost every conversation. He was discussing his aspiration to be appointed manager someday but could not resist adding “But I don’t know if I’m capable of that.” He chose a nice spot at a restaurant but kept seeking reassurance that it was okay. His date asked him why he kept doing that, to which he responded, “Because I’m not good at this stuff.”
Anatomy of insecurity
Most people look to a marriage partner as a support. The Torah refers to a spouse as an “ezer-helper.” Life is tough. Raising a family takes a lot. We look to marry someone who we feel can be a source of strength – to be our rock to keep us steady, not a stone weighing us down. Once we have that from our partner, we are very ready and able to give back in kind. We may therefore be uncomfortable with the thought of entering into a relationship with someone who we feel is dragging us down.
Most people also want to marry someone they are proud of. It isn’t so much about their many outstanding accomplishments and more about someone with good qualities. It is therefore unappealing to many when the person we are dating keeps trying to convince us that they aren’t worthy of respect and are actually rather pathetic.
Don’t let insecurity sabotage. It’s not the totality of who you are. It’s like a little monster inside your head. It doesn’t deserve to speak for all of you.
Secretly, the insecure person hopes the other will reassure them and help them feel worthy. Ironically, the opposite often happens. Instead of creating closeness, the constant need for reassurance creates discomfort. And because this usually begins early in dating—before goodwill has had a chance to develop—it can leave the other person feeling uneasy before they’ve had a chance to feel connected.
Very likely, this insecure behavior is being generated by a small part of the person’s brain and does not reflect the totality of who they are.
Often the insecurity begins with a small kernel of unworthiness. The resulting behaviors then trigger reactions that seem to confirm those fears, creating a self-reinforcing cycle. Over time, the insecurity becomes deeply entrenched—not necessarily because it was ever accurate, but because it has been rehearsed so often that it begins to feel true.
Insecurity can be – and often is – based on no real substance. All one has to do is imagine it, and for all intents and purposes it is.
Dating can make us more self-conscious
Then comes dating. Dating involves doing things that are easily affected by insecurity, from speaking to someone of the opposite gender, to opening up in a personal way with a relative stranger, to assuming responsibility for another person and an important relationship. What may be a relatively subtle issue elsewhere often becomes obvious during dating. And the other person will be affected by it.
Some people approach dating wondering, “Is this the right person for me?” Others approach dating wondering, “Will I be enough for them?” Those two questions lead to very different dating experiences. When a person’s attention is constantly focused on whether the other person likes them, whether they’re interesting enough, attractive enough, successful enough, funny enough, or simply enough—dating gradually stops being about getting to know someone else. The relationship becomes less about compatibility and more about validation.
When insecurity takes over, a person’s focus quietly shifts. Instead of asking, “What am I learning about this person?” they’re asking, “What are they thinking about me?” Instead of noticing whether they enjoy being with the other person, they’re trying to become someone the other person will enjoy being with. Ironically, the harder they try to earn acceptance, the less authentic they become—and authentic connection becomes much harder.
Effects of insecurity
Insecurity comes out in a variety of ways, and even the most insecure person may not display all types of insecure behavior. The main types of insecure behavior are:
- Self-deprecation. A habit of putting themselves down, both needlessly and excessively. Even small mistakes become reasons to criticize themselves. They struggle to accept compliments gracefully, often putting themselves down to avoid others doing it to them.
- People-pleasing. They’re prone to trying to fit in with whatever they perceive the other to prefer. They commonly suppress their own preferences and opinions to avoid disagreement, believing that even minor conflict could lead to rejection. They’re commonly overly apologetic, even when they did little to nothing wrong.
- Lack of confidence. They often defer decisions to others, assuming everyone else’s judgment is better than their own. They hesitate to express their needs and may even turn down kindness because they don’t feel deserving of it.
- Reassurance seeking. They put themselves down hoping the other person will reassure them. They’ll knock themselves in the hope that the other will build them up. The problem is that they’ll also undermine the positive reassurance by contradicting it and doubling down on their own negative self-image.
No change
Dating is not supposed to be a test of the other’s perseverance. It’s neither fair nor realistic to expect the other person to constantly push back against your insecurity. That quickly becomes exhausting, especially early in dating. As natural as it may feel, resist the urge to make them responsible for reassuring you.
The other is not (typically) looking to find fault. Most people begin a date hoping it will go well. They’re looking for reasons to connect, not reasons to reject you. There is rarely any reason to assume the person is interested in hearing you put yourself down.
How you feel doesn’t have to control how you act. In an ideal world, you would be free of insecurity and enjoy the experience of getting to know this person. You don’t have to wait until you feel confident before you can behave confidently. Your insecurity may be real, but it doesn’t have to dictate how you speak, respond, or show up on the date.
Do what helps the relationship, not the insecurity. The goal of a date isn’t simply to do what feels most natural or comfortable to you. It’s to create the best possible environment for two people to get to know one another. If insecurity is leading you toward behaviors that make connection harder, don’t let it make the decisions.
Accept a compliment graciously. If someone is dating you, there’s a good chance they like you. If they compliment you, it’s most likely sincere. Don’t contradict it; don’t deflect it. Just express gratitude and repay in kind.
State your preferences and opinions. Even if you’re not the most opinionated person, and even if you’re really easygoing, make a point of sharing your point of view or what you may enjoy.
Communication normally makes things better. If your insecurity slips out during a date, it can be helpful to acknowledge it rather than pretend it didn’t happen. A simple, “I sometimes put myself down more than I should—it’s something I’m working on,” often lands much better than leaving the other person to guess what’s happening.
Don’t be the other’s lawyer. Stop trying to decide for them whether you’re good enough. That’s their decision to make—not yours. Your job is to decide whether this relationship is right for you.
Don’t let one part of your brain sabotage the rest of it. Remember that insecurity is not the totality of who you are. It’s like a little monster inside your head. It doesn’t deserve to speak for the rest of you.
Insecurity is not your identity. It is simply one voice among many inside you. The goal isn’t to become perfectly confident before you date. It’s to recognize when insecurity is getting louder than it needs to be and gently turn the volume back down. Then let the rest of who you are show up too.
