Q: Hi, Couple. I’m a 20-year-old woman wondering if you have any advice for becoming a more confident dater. I do pretty well on dating apps, and I get plenty of invitations to real-life dates, but I find myself avoiding them because I become a nervous wreck before, during, and after every meet-up. The few times I’ve gone out with someone, I’ve found it difficult to enjoy myself because I was so worried that my dates would rather be elsewhere. My partners’ voices were practically drowned out by my own inner monologue asking, “Am I too quiet? Am I talking too much? Am I dressed right? Am I boring? Am I obnoxious? Will they want to go out with me again? Am I gonna get ghosted?” How can I stop my self-doubt and actually enjoy this time in my life? I need some dating advice STAT! – Self-Doubting Single, 20

Penelope’s advice: Like all life skills, dating takes practice

Hey Self-Doubting Single. First things first: you are SO not alone. Self-doubt often accompanies singlehood, especially for people who haven’t had much dating experience. I was there myself a few years ago, and I remember wishing there were some secret sauce that could deliver me instant dating mojo. But nope. Like any life skill, dating simply takes practice. The more you do it, the better you become at it.

That’s probably not the answer you were hoping for. Practicing dating means facing your fear head-on, which isn’t easy to do. But vulnerability breeds confidence. You have to be willing to put yourself out there – self-doubts and all – and accept that you’re going to make some mistakes along the way. That's exactly what I did. In my early twenties, my dating mantra became “fake it until you make it.” I stumbled my way through small talk, put my foot in my mouth more than I’d like to admit, and occasionally broke out in a flop sweat that even my kindest dates couldn’t ignore. And I hate to think of the hours I wasted overanalyzing every date-night interaction.

But you know what? After a few months of my self-prescribed “dating exposure therapy,” it suddenly became easier to carry a conversation. The chokehold of self-consciousness gradually loosened its grip. I spent less time wondering what my date thought of me and more time being in the moment. And I started scoring more second, third, fourth dates.

My dating confidence had been unlocked.

If a “full-length” date seems a bit too intense for you right now, speed dating is a great option for getting your practice on. You’re only with a person for a few minutes at a time, which makes each interaction feel lower-stakes. I obviously recommend Couple’s online speed-dating events, which are free and which you can join from the comfort of home, but there are also plenty of in-person events offered in most cities. Sites like Eventbrite make it easy to find local offerings.

However you choose to hone your dating skills, I wish you a pleasant journey of self-growth and self-love!

Andy’s advice: Stop worrying about the second date and stay in the moment

Hey, Single. While there are many approaches to developing your dating confidence, I want to zero-in on one area. During a first date, it sounds like you devote a lot of mental energy to worrying about whether there will be a second. While it’s totally natural to want to make a good impression on someone, focusing too much on the outcome of the experience turns it into more of a contest than an opportunity for connection, you know what I mean?

Try not to measure the “success” of a date by your ability to win over your partner. Dating is not a zero-sum game, and approaching it as such will only make you adept at twisting your personality into a pretzel. Plus, the truth of the matter is that there’s no way to mitigate the risk of getting rejected. The best you can do is be yourself and make the most of the moment in front of you.

Like Penelope said, adopting this mindset takes practice. “Be yourself” and “stay present” is fairly useless advice when you’re in the midst of a self-confidence crisis. The trick is to take it one step at a time. The first thing to do is to practice with the perspective that a first date is a worthy experience in and of itself, even if it doesn’t lead to a second. While your long-term goal might be a long-term relationship, a first-date flop won’t derail you indefinitely. That particular person just wasn’t the right match for you. Keep reminding yourself of that fact, date after date.

Once you can internalize that belief – once the pressure of “I MUST IMPRESS AT ALL COSTS!” is eliminated – I promise it will become easier to act like your genuine self. And with the focus off of “what’s next,” you can better enjoy what’s right in front of you.

And finally, if the issue of self-confidence isn’t limited to your love life, it might be helpful to work with a therapist or relationship coach to help you ground yourself in self-love before you look to share it with a partner. We work with many wonderful therapists and dating coaches (three of whom you can read about here: Kristi D. Price, Lisa Hawkins, and Tatoya Turner-Robinson). Coaches are fantastic resources for all singles on the dating scene.

M.J.’s advice: Remember that a bad date doesn’t make you a bad dater

Penelope and Andy made some great points about developing dating confidence, and I have only one more to add: remember that experiencing a bad date doesn’t mean that you are a bad date. There’s a lot that goes into making two people click – personalities, values, histories, chemistry – and none of that is one-sided. Does it hurt when someone rejects you? Of course. But that doesn’t make you intrinsically unworthy of affection. We all have our quirks. The trick is finding someone who’s compatible with them.

The thing about rejection is that it’s always going to suck to a certain degree, and admittedly sometimes it ain’t easy to shake off its sting. But make a conscious effort to avoid internalizing it and carrying it with you into future dating experiences. One person’s opinion is just that. Sure, occasionally a rejection might reveal a hidden truth about yourself that you need to address – for example, I once was told by a date that they really liked me but that they couldn’t imagine a future with someone who chewed with their mouth open 😲 – but we can't let those moments pull us down into a spiral of self-doubt.

At the end of the day, dating is a numbers game. Maybe you’ll get lucky and find someone you click with right away, but for most of us, it takes a lot of trial and error to find someone whose peccadilloes coexist beautifully with our own. Embrace the journey, embrace your quirks, and confidence will soon follow.

Wishing you the best out there!


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