Dear Confused Dude: Here's Why You Didn't Get a Second Date

You worked up the nerve to ask her out for coffee (probably your first mistake -- I judge guys who ask me out for coffee). Maybe even a cocktail. And you thought everything went well... but then she totally ghosted. And you're so confused.

So, based on my experience -- as a person, as a woman, as a matchmaker, or as a supportive friend -- here are some likely ways you blew it.

1. You tried to kiss her. 

EW! NO! WHY??? YOU DON'T EVEN KNOW HER!!! WHY WOULD YOU TRY TO KISS SOMEONE YOU DON'T EVEN KNOW???!!!

As a blogger, I forgive you. You probably don't know any better. You've probably been brainwashed by some douchey pickup artist type -- or even by some silly Hollywood movie -- to think that you "should" kiss the girl. 

If you like this girl and you want to see her again, you won't try to kiss her until you actually know her. Otherwise, she's going to think you're some perv who goes around trying to kiss every girl you've ever had a cup of coffee with. She's going to think that kissing doesn't even mean anything to you. For me, that's a total major deal breaker. For me, just holding hands is intimate and special -- something I wouldn't want to do with a person I don't know and don't feel any affection for. 

Which is why, as a woman, I don't forgive you. If you try to kiss me on our first date, you are someone I will never talk to again. Yes, that means I'm probably going to ghost on you. In another situation, I might say that ghosting is rude. But if you try to kiss me the first time we hang out, you don't deserve an explanation from me. I've wasted enough time on you already.

Still confused? Try to think of it like this: this girl is pretty, right? That's why you asked her out -- at least partly. You think you're the only guy who wants to kiss her? No! Dudes try to kiss her, like, every single day. If you want to stand out, show her that she's more than a set of lips to you. If she went around kissing every dude who wanted to kiss her... she'd be kissing hella toads.

Want to know more? Check out Women: Instantly Improve Your WHOLE Life By Learning This ONE Phrase.

2. There was no connection, because you asked boring or contrived questions.

A lot of people -- male and female -- have a way of making a first date feel like a job interview. "Where are you from?" "What do you do?" "Do you have any siblings?" "Where did you go to school?" "What was your major?"

BORING. 

If we spent an hour doing that, I wouldn't want to see you again. There would be no reason to. A night at home with Netflix would be a lot more exciting.

Then there are people who show up with this whole script: "If you could only eat one thing for the rest of your life, what would it be, and why?" "If you could travel anywhere, right now, where would you go, and why?"

These questions don't feel natural at ALL. If someone asked me a question like this, I would feel weird about it. It would also make me think there was no REAL connection there, because, if there were, you wouldn't be asking me a memorized list of questions -- we'd just be talking! 

So where's the middle ground? What should you do or say or talk about if your greatest fear is running out of things to talk about? You could try:

• Planning a date that involves an activity. Maybe go to a boba place with board games, a bar with skeeball or basketball games (or just go to Chuck E. Cheese -- you'd get SO many cool points from me if you wanted to play games with me instead of just guzzling drinks), or a lake with peddleboat rentals. Start with an activity you can complete in about an hour before suggesting a weekend retreat, though.
• Asking questions based on what she just said, instead of going down a mental list. For example:

Her: OMG, sorry I'm late! I just got back from a trip, and I'm so behind at work.
Him: A trip? Where'd you go?
Her: Portland, for work.
Him: Nice! Did you get a chance to explore while you were up there?
Her: (Talks about stuff she did in Portland.)
Him: That sounds awesome -- I'll have to add it to my list. But first, I'm going to check out San Diego. Warm water, great waves, and microbrews! Have you ever been?

• If you MUST show up with a prepared list of questions, at least try to pick ones that are neither boring nor contrived-sounding. If I HAD to make a few suggestions, they would be, "What is your most outrageous travel story?" or "Have you been following the debates? What did you think about ___?" (Whoever said not to talk about religion and politics in polite company... was probably really boring.)

3. There was no connection, because you don't have good social skills.

Did you listen attentively, or were you half listening, half thinking about work? Did you ask her questions about herself, or did you just ramble on and on about yourself? Did you make good eye contact? Did you lose yourself in the conversation, or get hung up on what you're going to say next? 

The good news about having bad social skills is that they can be improved. As I wrote in These Specific Behaviors Will Make You More Charismatic - Starting RIGHT NOW!, 

Some people unconsciously "learn charisma" on their own. But others (including Steve Jobs) might have to consciously decide to study it on their own. 

So instead of wasting time memorizing a list of ways "pickup artists" manipulate women, actually improve your social skills. If you read The Charisma Myth: How Anyone Can Master The Art and Science of Personal Magnetism, you will learn how to get along better with strangers, dates, friends, colleagues and family -- without ​being inauthentic. 

4. You showed up looking like shit.

Want to NOT get a second date? Wear a t-shirt on your first one.

This is probably more true for older folks than younger ones -- but whatever your age, it's sort of rude to show up in a t-shirt or ten-year-old jeans. Because, meanwhile, your date has picked out a cute outfit, done her hair and put on some makeup​. So show some respect and put on a button-down. Or whatever men wear when they're not thirteen anymore. 

I know you're terrified of coming across as "desperate" or "trying too hard." I know you might even live in the Silicon Valley, and you think wearing a t-shirt makes you "cool." But I know a shocking number of women who have refused  a second date because the guy dressed too casually on the first one. 

5. You did everything right, but there still wasn't a connection, because not all people are soulmates.

Sometimes, people find each other physically attractive... but they're just not attracted to each other. Sometimes, you were perfectly funny or smart or charming, but your date just didn't feel that click with you. 

That sucks -- but remember: love is a numbers game. You aren't going to date the vast majority of the people you meet. You're probably only going to fall in a love a few times in your whole life. The best thing you can do is keep putting yourself out there. Keep making eye contact. Keep making new friends. The more people you meet, the more women you ask out on a date, the more likely it is that you're going to build something meaningful and develop feelings for each other.

***

There could be another reason you're not getting second dates. One good way to figure out what you specifically are doing wrong is to ask friends you trust -- or even a therapist. I've found that a lot of people (of both genders) have learned maladaptive behaviors that hold them back in dating. Getting to the bottom of yours could improve your love life (that is to say, your life​) immensely.