Living on a college campus for the past four years has left me in a dating desert. Actual “Hey, let’s go out on a date!” offers have been few and far between. Still, I have been on a few dates—good ones, bad ones, and ones where I wanted to leave immediately and bleach my eardrums just so that I could unhear what had been said. Hopefully you can learn from the mistakes that guys have made while trying to get cozy with Yours Truly.
1. Not asking her on a real date.
Asking her to join you and 10 of your closest friends is not a date and you will not get to know her any better. Even if it’s just you two grabbing dinner, it can still be ambiguous as to whether it’s a date or not, so be direct and straight-up ask her out. Because we ladies get so few offers for real dates, confidently asking her out will: a) confirm that you are truly interested in her; and b) assure her that you are a confident grown man who knows how to have a relationship that extends beyond this weekend’s bar specials.
2. Being a scrub.
To quote the ancient philosophical school of TLC:
I’m lookin’ like class and he’s looking like trash/
Can’t get with no deadbeat ass.
If you asked her out on a real date, you can bet your fedora that she’s gonna be spending at least 45 minutes picking out her outfit. Nothing says I’m not serious about you more than showing up in basketball shorts and a dirty T-shirt when I’m wearing killer heels and no underwear.
Unless you’ve specified that you’re taking her to a fancy restaurant, rock-climbing, or somewhere else that has a set dress code, you should be wearing a dress shirt and either dark wash denim or dress pants.
Yes, both the shirt and pants have to be clean.
3. Making money an issue.
One of my biggest anxieties on a first date is the check. It’s not about who actually pays, it’s about deciding who is going to pay for it.
I usually go by the maxim that if you invite someone out to dinner or drinks, you should be the one who is expected to pay. Yep, when I ask dudes out, I cover the meal. If you would like her to split the bill (or need her to, I get it, I’m a broke 20-something, too), then say something as soon as it’s relevant. You don’t need to tell her the first moment you see her pretty face, but you should definitely tell her before she awkwardly reaches for the check.
I cannot stress this enough—pick a place or activity that is comfortably within your budget. There is nothing worse than watching a guy sweat when he gets the bill. If you can’t afford a fancy restaurant, take her on a picnic (that shit is romantic as hell) or to a food cart in a really cool neighborhood. Quirky alternatives establish you as someone who is creative and interested in showing her a genuinely good time and not just another unoriginal schmuck.
But whatever you do, do not take her to Taco Bell. You are not 14.
4. Getting absolutely sloshed.
So now we’re out on a real date and I’m nervous, you’re nervous, what do we do? Grab a drink. That’s cool. Two drinks per person maximum. Not only will this save your wallet, it will also save face for both of you. You think it’s going to loosen you up so you can get to know her better, but when you’re so messed up that you’re literally under the table, it tells her that you’re not good under pressure and that you might have other underlying issues. I found this out firsthand after going out on a date with one of my college friends—he got so messed up that when I tried to close his drunken, slack-jawed mouth, he mistook it for an invitation to kiss me…yeah, we haven’t spoken since.
5. Emotional vomit (AKA oversharing).
Going out on a date is all about getting to know a girl to see if you wanna spend more time with her. Ask intriguing questions that help you learn more about who she is. Share parts of your life with her—but not all of it.
Whatever you do, please please please this is not the time to tell her about your cross-dressing pantyhose fetish or that you took a Viagra when you hit the bathroom just in case. (These were actual overshares I encountered from one poor soul over the course of one bad date.) While these things may be a very real part of your life, they are not selling points for a first date. They are mildly terrifying and will leave the girl questioning whether you’re going to ask to try on her knee-high socks later.
While sharing extremely personal aspects of your life is good for building relationships, it has to be done in a way that is mutual. That means everyone involved is emotionally and mentally prepared to handle the #realtalk you’re about to drop on them.
Good luck, my friends, and may your next date be the first of many more to come.