How to Have More Confidence in Dating - Justin Lioi, LCSW - Brooklyn, NY

For a good majority of people out there dating has never been easy. Many would say it’s not even fun. And if you’re still on OKCupid or Tinder or name-your-site after many, many years you may have lost your confidence in dating. How can you get that back?

Shifting Expectations

While you’re sitting at the bar or coffee shop, waiting for your date to arrive (I recommend not doing dinner or something that may keep you longer than you want to be with someone if you’re meeting them for the first time) what is going through your head? Aside from the nerves you might feel, I want you to honestly think about your expectations.

If your thoughts are focused on “this person is going to be The One” instead of “let me slowly get to know this person”, well, you have very little chance of really connecting to who they are. This will have your judgment gear out—scrutinizing your date while missing the whole of who they are. You might be very focused on certain aspects that you want in a person, but are you missing the proverbial forest for the proverbial trees.

Online dating already takes some exciting surprises away from us—I often hear about how someone has a specific characteristic in mind (e.g., height), but then ends up with the opposite. The internet doesn’t really give you a chance to meet that unexpected person.

So find a way to be excited for the half-hour journey of getting to know someone and being surprised by something you didn’t expect.

How do you do that?

Refocus Your Energy on Them

On a first date, like a job interview, people spend a lot of time wondering how they are coming across.

Clients talk about this all the time for times other than a date. They’ll describe how they are constantly trying to figure out what the person they are talking to is thinking about them.

Wow, that’s a lot of wasted energy!

Plus, there’s usually a lot of energy spent on not allowing their own quirks to come out. Their “bad” habits.

Again—a lot of wasted energy.

That’s a lot of energy that is NOT going into getting to know someone else. Figuring out whether you like them. Whether they’re interesting. Whether they’re funny or have an amazing quirk of their own.

What keeps you focused on you when you’re on a date with them?

Developing the Habit of Curiosity Can Increase Your Confidence in Dating

Here’s what you need to do to build your confidence in dating. Make it fully about the other person. Figure out how you came across later. Spend the date becoming insanely curious about who they are, what they do, why they do it.

Ask questions. Ask more questions.

Show how interested you are in getting to know them.

If, after forty-five minutes you’re bored out of your skull then say, “It was nice meeting you, but I need to get going.” (Don’t ghost!)

Why start to get anxious about what they think of you before you know whether you want them to like you?

Now don’t get me wrong. Don’t be weird, don’t be evasive if they ask you questions, and don’t be mean. Learn to enjoy the process of dating.

Just focus on them.


Confidence in dating can come down to expectations. And expecting this to be The One is expecting too much. Like the beginning writers who are taught the purpose of the first sentence of the novel is to get the reader to read the second sentence, your job is to reverse that and see if you can learn enough about the person to know whether you want to go on a second date with them.

Confidence in dating can become a non-issue when it’s really about getting to know the other person. This takes a small shift in focus. If you’re struggling with getting out of your own head for this, though, you’re not alone. If you’d like to talk more individually, don’t hesitate to shoot me an email and we can schedule a FREE 15-minute phone session.

Justin Lioi, LCSW is a men’s mental health and relationship expert. He is a Brooklyn therapist (as well as also seeing clients online throughout New York State and internationally.) He received his degree from New York University and has been working with men and their families for over 10 years. Justin is on the Board of the National Association of Social Workers and writes a weekly column for the Good Men Project called Unmasking Masculinity. He can be found on local and national podcasts talking about assertiveness, anger, self-compassion, all with the goal of becoming the man you want to be.