How to Reassure an Insecure Date

Why is it that some of the most amazing women don’t realize how great they are? I’ve had conversations with a few of my guy friends, and it seems that insecurity is a dating epidemic.

As a chronically insecure over-thinker I can tell you that it’s hard to let go and just enjoy the dating experience. It’s taken me many years to understand what I need from a partner to feel comfortable and the kinds of behaviour that make things worse.

Here are a few of my suggestions on how to reassure an Insecure date.

Be Steady and Consistent

If your date is anything like me, her insecurities will make her over-think everything you say and do. I know, that’s a ton of pressure, but just remember, she’s not doing it on purpose. You can make things way less stressful on both of you by staying calm and keeping your word.

If you have plans to meet at a certain time, be there. If you make plans to call her, don’t flake out. And don’t stop texting her halfway through a conversation. She’ll take it as an indication that you’re angry or disinterested, even if you’re just busy with something else.

Be Open to Talking about Her Concerns

Hear her out. Sometimes just talking about things will be enough to alleviate her anxiety. Try not to discount or minimize her feelings. You might know that you’re into her and that you want to date her and see where things go, but she might not believe it right away. By encouraging her to open up about her fears, you’ll help her to feel more comfortable and that will help her relax into things.

Be Kind

Don’t lose your patience or make fun of her. Don’t tell her she’s acting crazy, or that you’re tired of having to reassure her.

If you feel that the burden is too great, it’s better to break things off than to make her feel guilty about her issues. It’s that kind of reaction from past partners that probably solidified her feelings of insecurity in the first place, and it won’t get her any closer to trusting you.

Be Real with the Compliments

You might think that piling on the compliments is all you need to do to make your date feel good about herself, but it’s not that simple. You can tell her she’s beautiful and amazing a million times and she won’t believe you, especially if you’re not being 100% genuine.

People who are insecure tend to have highly tuned bullshit detectors. That’s because they’re always scrutinizing things like eye contact and body language to figure out what you really mean. Compliment her only when you’re really feeling it, and she’ll probably start to relax a bit more.

Don’t Force It

No matter what you do to try to make your date feel more secure, she’s the only one who can convince herself. It might take some time for her to get there, so have patience. If the whole thing seems way too high maintenance or intimidating to you, don’t string her along. Move on so that she can meet a guy who’s willing to put in the effort.

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