How Do I Get Better At Dating Without Being Cringe?

Estimated reading time: 15 minutes

Dear Dr. NerdLove,

I hope this email finds you well. I’ve been an avid follower of your insightful advice on relationships and dating, and I find your perspective immensely valuable. I am reaching out because I’m grappling with a particular challenge in the realm of dating that I believe you could shed some light on.

The dilemma I face is that, like any skill, dating requires practice to improve. However, unlike more tangible skills such as playing the piano or learning to dance, dating is fundamentally a people skill. This uniqueness poses a concern for me – the inevitability of encountering awkward interactions and the fear of being labelled a creep or, worse, ending up on a cringe compilation.

While I understand that some level of discomfort is part of the learning process, I’m eager to navigate this journey without becoming a source of amusement for others. The prospect of being featured on a “cringe Pick Up Fails” video on platforms like YouTube or TikTok and having content creators like “Moistkritical” dunking on me in a 20-minute video, while I become the laughing stock of the internet is particularly daunting.

I would greatly appreciate any guidance or strategies you could offer to help me refine my dating skills while minimizing the risk of ending up in cringe-worthy situations. Balancing the need for practice with the desire to avoid negative labels seems like a delicate tightrope, and your expertise would be invaluable in finding that equilibrium.

Thank you for your time and consideration. I look forward to any insights you can provide.

Best regards,

Dammed If I Do, Dammed if I Don’t.

Can I ask you a serious question, DIDDID? Just between you, me and everyone reading this … is showing up on someone’s TikTok or cringe compilation really what’s holding you back?  

I realize this sounds dismissive, but I’m being serious here. If someone were to hold a gun to your head and tells you that if you don’t give the real, 100% honest answer to the question, they pull the trigger, that you would still say that YouTube and TikTok creators are the reason you’re not talking to people you find attractive?

Because, if I’m being honest? I think that’s an excuse. I don’t mean that it’s not something that you worry about, don’t get me wrong. But I think that’s the story you’re telling yourself to give yourself a permission structure to not try.

It’s not that there aren’t channels and creators who make fun of people for content, including people who are out there trying to find love and going about attempting to meet people in good faith. And it’s not like there aren’t people who seem to only be going on dates so they have material to talk about on TikTok. But in a country with millions of single women, in cities with tens to hundreds of thousands of people you might be interested in dating… you sincerely and seriously think that the odds of you ending up fodder for someone’s channel are high enough that it’s an actual risk for you?

Or – stick with me here – is it that you’re afraid of the rejection? Would it be more accurate to say that you’re actually worried that nobody would be interested in you, that your attraction to someone would be taken as an insult and you worry about their judgement? Would it be more accurate to say that it’s easier to dress this very common fear up in a mask of becoming a national spectacle instead because it’s easier to point to that and say “I dare not?”

So, real talk time. I get a lot of letters from folks who convince themselves that dating and attraction is somehow supposed to be a frictionless experience, where everyone else is able to navigate the world of meeting people and interacting with them so fluently and so smoothly that it seems more like watching highly dexterous acrobats performing an elaborate dance, while they stumble around and blunder into people and create a mess. They have talked themselves into the idea that they are such uncouth, unsocialized goblins that the slightest misstep will forever brand them as The Unwanted and they’ll be condemned to die alone and unloved because the word will reach any and all that they dared to present themselves as a suitor to the princess. Any princess. Or duchess, baroness, countess, lady-in-waiting or even random scullery maid for that matter.

And funny thing: human interaction in general has never been a frictionless experience. There has never been any sort of contact between two or more people that doesn’t have some degree of friction inherent in it. People stumble over their words, say the wrong thing, trip over their own two feet or give the wrong impression all the time and yet they’re not bundled up and sent to live forever on the Island of Misfit Toys. People in general understand that being human is to be flawed, that mistakes happen and nobody – nobody – is immune to shoving their foot in their mouth.

And honestly? 9 times out of 10, people who are on the receiving end of those mistakes either don’t notice or don’t care. I’m sure that you, DIDID, have had times when someone was talking to you and accidentally said something weird or did something cringey and you just let it go by like it was no big deal. Because it wasn’t.

So why would you assume that other people aren’t capable or willing to give you the same grace that you’ve given others? Why wouldn’t you give that grace to yourself?

I presume that you have people in your life that you hang out with, friends you spend time with and who enjoy your presence. I similarly presume that you are able to go about your daily existence without managing to be thrown out of restaurants for being disruptive, order drinks at the bar without having drinks thrown in your face for being rude to the bartender and otherwise manage to get through life without being chased by an angry mob.

If you can manage that, you can manage to talk to people you’re attracted to without ending up on a watchlist somewhere. I promise you: you can.

The problem is that you’ve convinced yourself that none of this actually counts or matters and that the skills needed to make friends are somehow different from the skills needed to meet someone you might want to date or who might want to date you. And they’re not. They’re the same skillset. The only difference is the end result you’re looking for.

There is no form of meeting people and dating that doesn’t come with the risk of friction and stumbling over yourself. But that doesn’t mean that it’s impossible or that you need to give up until you’re slicker than a freshly greased weasel.

Here’s the thing: at risk of coming across as “Old Man Yells At Cloud”, a lot of people have gotten too reliant on doing all of their interacting with others at a distance. Yes, I’m going to be That Guy and say that we have all gotten far too used to conducting our lives – that people have forgotten that “go outside and touch grass” means stepping away from the screens and realizing that doing all of your socializing in the digital realm is unhealthy.

(Please notice very carefully I said all socializing, not “never use your computer to contact another human ever”.)

There are three issues here. The first is that mistaken belief in a frictionless experience that I mentioned earlier. The second is that social skills are skills and all skills are improved with actual use. And the third is that relying on the people in your screens for all forms of human contact means that you tend to forget that very little on social media is authentic and organic. Leaving aside the carefully curated versions of themselves that people present online, there’s also the fact that so much of what you’re professing to be afraid of is artificial. You’re getting fed material by an algorithm that is designed to see engagement as the alpha and omega and there’re few things that get more engagement than laughing and pointing at someone else’s cringe. And if there isn’t any real cringe there… well, point and laugh hard enough and people will assume anything is cringe.

So what do you need to do? Well, I’m going to tell you what I tell people all the time: get the fuck off the Internet. Quit watching social fearmongering TiktTok videos from people who want to stigmatize any and all human interactions, unsubscribe and downvote channels that thrive on third-hand embarrassment, unsubscribe and leave all the subreddits and image boards that keep telling you that if you put a toe wrong, you will be subjected to the Five Minute Hate and go outside and touch grass.

It’s admirable that you don’t want to make people uncomfortable. It’s understandable that you don’t want to be a creeper. But you’ve taken reasonable positions – I would prefer not to upset people – turned it to 11 and snapped the dial off.

If you want to get better at dating, you have to practice your social skills. And the only way you can practice your social skills is to go out and socialize. You have to go out into the world and interact with people in person. There is no substitute for this, no way of short-cutting things, nor a way to avoid any and all risk of rejection or saying something stupid. Because you will. You have before, and you will again. So has literally everybody else out there. There is no person on this earth who has never said or done something that has made them want to dig a hole and pull it in after themselves. The most charismatic people you can think of have said the dumbest fucking things in front of people they were hoping to impress or connect with. The funniest comedians you have ever seen have bombed and bombed hard in front of audiences.   

The difference is that the people who are socially skilled know that mistakes aren’t fatal, nor are they apocalyptic. I have had times where I have quite literally choked – I aspirated on my own saliva – while talking to incredibly hot women. And while that was embarrassing in the moment, rather than running away and getting plastic surgery to disguise myself before moving to another country, I laughed at it. I made a joke about the awkward and the moment went from being embarrassing to charming and I got their numbers.

Part of why you need to practice your social skills is so that you don’t make as many mistakes as you might without practice. But another part is to learn that not only are mistakes not fatal, but you can recover from them… often quite easily.

And here’s another important thing to consider: the folks who get labeled creepers – actual creeps, not “dude who said the wrong thing once” or “dude who asked someone out and got turned down” – aren’t people who made innocent mistakes or stumbled over their words. They’re people who persistently disregarded other people’s lack of interest or discomfort. Women aren’t out there looking to zing you for daring to talk to them; they can tell the difference between someone who’s a little nervous and got tongue-tied and someone who is aggressively odious or incapable of reading the room. And frankly, most will give you room to recover when you can show that you’re being mindful of their comfort.

If you want to improve your dating skills, then the best thing you can do is go outside and touch grass. Take the things that you love doing and find places and opportunities to do them with other, likeminded people. Talk with people in person, make jokes, make friends, share stories and bond over shared experiences, interests and values. Invite your new friends to get coffee and hang out, throw parties, bring people over for backyard cookouts and board game nights.

All of the socializing, conversing and connecting that you will be doing will be helping you polish the skills you need to find a date. Because if you do this consistently, you’ll almost certainly meet women who you think are kinda cool and that you enjoy talking to, and they’ll feel the same. And it will be perfectly natural to say “Hey, there’s $A_COOL_THING happening this weekend, and I think you’d really enjoy it. If you’re down, I’d love to take you”.

Do that a few times and you’ll soon realize that you’re actually dating, and dating rather consistently at that.

But you have to be willing to let go of the fear of being someone’s cringe-fodder and just get used to existing in the world – as friction-filled and abrasive as it can be at times. I promise you: it’s not the nightmare that you’re convincing yourself it is. It’s just unfamiliar… and you can change that. You just have to decide to take those first steps.

You’ll be ok. I promise.

Good luck.

Hey Doc,

I’m 22M and I have a crush on a woman (23F) from my university  and we were quite good friends when, for some reason, I started developing feelings for her after I broke up with my ex.

I asked her out last September but she said her priorities are different at the moment (she might still be hung over her ex) and so I knew better and stepped out.

She had always been on my mind but I made sure not be too desperate for her attention, or ask her out again for that matter.

Cut to two days ago, we hung out with a common group of friends where she said she’ll dedicate “We don’t talk anymore” by Charlie Puth (as poking fun about the fact that we really didn’t talk a lot since I have been avoiding her thinking it might help with my feelings). She asked me how I was and if I still felt something for her and she said if it is ever to happen, it will, even if it’s 10 years apart. She then proceeded to say to talk to her and promised that nothing will be awkward between us.

While on the outer side, she shows how indifferent she is to the fact that she’s dating nobody, it’s clear from her online presence that she’s not over her ex. She comments something really clingy on her ex’s posts and he supposedly replies as well (He is in a relationship as far as I know) and she keeps posting songs and statuses aimed at waiting and fixing things with her ex.

All of this has put me in a spot as she’s the woman I’ve always wanted to pursue and hoped to date to marry even. But all of this really puts me out of perspective as to how I might not even get a chance to be a part of her life.

I am so stuck in this dilemma about how to act around her and how do I see myself through this situation and if something can work out between us. Can anyone please help me out?

Against All Odds

Alright, my dude, I am going to try to do this as gently as I can: you’re missing your chance to be a part of her life right now, because you seem to be missing what she’s telling you.

Right now, she’s telling you that she misses you and that she’s sad that you’ve pulled away from her. She’s doing her best to be gentle with you and considerate of your feelings, telling you that she wants you in her life, that it’s ok that you’ve got a thing for her and she cares for you deeply.

I want to emphasize that: she cares for you a lot. It’s just that she doesn’t care for you the way you’d prefer. That’s not a bad thing. If anything it’s good. It says that she’s a caring and considerate person, someone with a lot of emotional intelligence and maturity mixed with compassion and affection. That’s someone you want in your life, the kind of relationship that can be really significant to you.

She does love you, my dude. It’s philia, the authentic and abiding love of a dear friend, an important and significant person in her life, not eros, but it’s still love and it’s still valuable and meaningful. It’s not a consolation prize, nor is it lesser just because it’s not romantic or sexual.

But right now, you’re not seeing that. You seem to be in a place where you’ve convinced yourself that the only way you can or should have her in your life is as a romantic partner and you’re putting so much emphasis on that that you’re missing the forest for the trees. You are building her into something she’s not and you’re pulling away from her because of that. As wonderful as she is, I can promise you: she’s not the only person you can or will love. She’s not the only person you’ll ever want to date, and I can definitely tell you that she’s not the only person you could ever be with.

Now I will tell you this part, knowing that you’re going to dismiss it out of hand: you are young. You are inexperienced and you’ve barely seen any of the world yet. I can tell you – from experience – that while you have the fantasy of marrying her, that’s not the same thing as actually knowing that she’s someone you want to settle down with. You are in love with your idea of her and missing the actual person underneath.

And here’s the thing: this has nothing to do with her being hung up on her ex or being deep in her feelings about it. That’s separate from her relationship with you. Even if I were to snap my fingers and she would suddenly be over him, that wouldn’t mean that she’s going to leap into your arms. It’s possible to love more than one person at a time, and she does love you. It’s just that you’re focused on one kind of love when she’s offering you a different one. And you’re at risk of missing that.

What you need to do is let the fantasy go. Recognize that the feelings you have are just that: feelings. The intense limmerent nature of them will ease up and fade once you stop engaging them. And if you can do that and see her for who she is and recognize what she’s asking for and what she’s offering, you and she will have a much longer and more meaningful connection than you are imagining. As you get more experience and mature, you’ll look back and see that.

Right now, you’re focusing on the lack and the “loss” – the idea of how to be with her and the knowledge that it isn’t going to happen the way you want it to in this moment. Avoiding her isn’t making those feelings go away, because you’re not letting the feelings go. You’re just pressurizing them, compressing them, concentrating them and ensuring that they’re taking up the forefront of your mind. What you need to do is see them, acknowledge them and then turn your attention elsewhere. If you stop trying to either force the feelings away or trying to figure out how to change her feelings, then the limerence will fade and you can get back to having your friend again.

She’s told you what to do. She’s said, straight up, what she wants from you. She wants you to be there. She wants you to talk to her. She wants you in her life. She misses you. You miss her. She sounds like a pretty awesome person and an awesome friend. Don’t screw up something great just because it’s not the precise flavor you’re hoping for.

Good luck.