How to Build Confidence in Dating & Overcome Natural Insecurities

Boost your confidence in dating and overcome insecurities whether you're going on a first date or exploring a relationship with someone new.

In the world of dating, confidence is the key that unlocks countless possibilities and leads to fulfilling connections. It’s an intangible quality that radiates from within, capturing attention and inviting genuine attraction. But confidence in dating isn’t an easy thing to develop and maintain, especially when it can feel like there’s so much at stake.

Learn how to embrace your authentic self and overcome romantic jitters by

Making a list of questions for the first date
Doing something you love before you go on a date
Planning an activity date
Focusing on positivity
Wearing clothes that make you feel great
Lowering your expectations
Using a matchmaker
Prioritizing your independence

Whether you’re embarking on a first date, in the getting-to-know-each-other stage, or navigating the complexities of a blossoming relationship, this list of strategies for building dating confidence will propel you toward personal growth and meaningful experiences. Now let’s get to it!

Make a mental list of questions

Calling all introverts: If you’re nervous about what to talk about on a first date, stick to the question game. Coming up with a mental list of questions to ask your date is a great way to build your confidence in dating, especially when you’re prone to crippling shyness with people you don’t know well.

Before you go on a date, think of at least five questions that you can ask if an awkward silence is impending. (Hint: You can use our list of conversation starters as inspiration.) That way, you’re prepared if the conversation starts to fizzle or you’ve both exhausted a topic.

You might not be a talker, but you can ask questions to get the other person to start chatting. Doing so will hopefully lead to discovering shared interests or at finding a topic that you can both talk about with ease.

Prep for the date by doing something you love

Pre-date jitters are natural. Being nervous before you do something nerve wracking (like meeting someone new) just means that you’re human. But sometimes these jitters can keep you from being yourself. So, how do you combat these anxieties and start building dating confidence?

Do something that brings you peace or joy before you go on a date. A winning activity is exercise because it releases endorphins that can help to reduce stress. But do anything that you love to do, like painting, yoga, running, belting it out in the shower—you get the idea. Then, when it comes time to get ready for your date, you’re already in a good head space.

Plan an activity date

If you’re still worried about overcoming insecurity about keeping up a conversation, take it upon yourself to plan a date that involves an activity. There can be a lot of pressure on dinner and coffee dates, where all of the focus is on each other. Why not try a hiking date or a mini-golf date instead? When you’re physically focusing on something else, there’s less pressure to keep up constant conversation.

While this might not directly boost your confidence in dating, it will help you ease into meeting someone new and make the art of conversation not so scary.

Focus on positivity

If you ever feel frustrated with the reality of modern dating (like dating app fatigue, ghosting, post-pandemic baggage, etc.), try to refocus your thoughts on the positives. One of the best ways for building dating confidence is reminding yourself of the good. The good in other people, the good that you’ve experienced in dating past, and, most importantly, the good in you.

Build yourself up by writing down a list of what makes you great. What are the things you love most about yourself? What strengths would you bring to a potential partnership? What do people say that they love about you? Remember this list if you’re ever feeling insecure.

Wear clothes that make you feel great

One of the key steps in dating is to bring your best self to the dating relationship, no matter how new it is. This means dressing for success. (And no, we don’t mean wearing a suit to every date.) Bringing your best self involves putting on clothes that make you feel great, powerful, sexy, you name it. When you do, chances are that you’ll exude confidence. Dress for the occasion, of course, but make sure that your outfit is something you feel comfortable and really darn good in.

Lower your expectations

Ok, you might be thinking, “Why would I lower my expectations for meeting a potential partner?” Let us explain.

The world of dating is complex and full of societal and internal pressures. A way to have more confidence in dating is to lessen those pressures by lowering your expectations of the date itself, the person, and the outcome.

Try to live by the mantra, “high hopes, low expectations.” Basically, be hopeful about and visualize having a great time and experiencing romantic interest, but leave your expectations about what will happen at the door.

Use a matchmaker

Sometimes people need a little extra help in the dating arena. That’s where a matchmaker comes in. Matchmaking services, like Tawkify, provide feedback, guidance, and other post-date insights that can help you identify areas that you can work on to help you start dating with confidence again.

Remember that rejection is part of life

One of the biggest insecurities in dating is the question, “What if they don’t like me?” Humans’ fear of rejection begins at a young age—we want security, community, and love. It’s only natural that we’re afraid of losing it. But don’t let that stop you from putting yourself out there.

Whether you’re looking for casual dating vs. a serious relationship, remember that being vulnerable is powerful. Speak up for what you want and need without worrying about if the person will accept you.

Plus, when there is less fear of rejection, you’re more willing to follow up with a text or ask for a second date. You never know if you don’t try. The more times that you practice vulnerability, the easier dealing with rejection will be. Why? Because you can move on knowing that you did your best and took a risk for the possibility of love.

Prioritize your independence

Many people’s dating insecurities stem from a fear of being alone or having been single for a while. Remember that dating with confidence starts with you. That means thriving in your own bubble of independence. Focus on your career, take time to travel, sign up for group events in your city, or wine and dine yourself on the weekends. Whatever independence looks like for you, lean into it. Feeling comfortable in your own independent skin will help you develop a sense of self-assurance—that you don’t need someone else to make you “whole.”

It’s easy to see why confidence is attractive. It helps you be your best and truest self around others, become less fearful, and remind dates that you’re a strong, independent person. When you use these strategies to overcome insecurities, you’ll develop confidence in dating that will last a lifetime.