Dating Rules For Men: The First Date Guide

First Date. Simultaneously the most terrifying and exhilarating pair of words in the English dictionary. For every first date that has gone well, five have gone worse than a Malaysian Airlines flight. So I polled every girl in our office with the simple question, “what was the worst first date you’ve been on?” to create these five dating rules for men.


Rule 1: Always Pay On A First Date

➢ If you take a girl out you need to pay, especially on the first date. No girl likes someone who is cheap. Keep in mind you can have affordable, fun first dates but not be cheap. A coffee date or a day in the park make for great dates but you gotta pay for them. These are dating rules for men and men pay for their dates.

Delilah: “I went on this one date to the park, we got Waffles and Dinges and he didn’t even buy me a waffle!”

➢ Clearly this guy didn’t get a call back. If this guy just spent $3 more he probably would be on a second date now, instead he’s getting left on read. I asked Delilah for the guy’s number so I can send him the dating rules for men, she said no. 

dating rules for men quote

Rule 2: Show Some Effort

➢ You already got through the hardest part, getting a date. Don’t mess it up by acting like you’re too good for her by showing up in sweat pants. Be a big boy, wear some jeans, a nice shirt, and shave.

Nicole: “He showed up in sweatpants, a really bad jacket, and this terrible, mushroom haircut. He probably asked his barber ‘make me look horrible.’ He still texts me too.”

Me: “Do you respond?”

Nicole: “Never. It’s been two months.”

➢ Three key takeaways from Nicole.

1) Dress like an adult and put some effort into your appearance.

2) Don’t get a haircut before a date.

3) TAKE HER HINT. If she isn’t into you don’t be a creep. Go find the next one.

➢ Need a little inspiration for your big first date? Pair this stunning blue plaid blazer with a clean pair of jeans to make a lasting impression.

dress up; dating rules for men

Rule 3: Plan Ahead

➢ This goes with Rule 2, put some thought into the date. Have an idea about what you want to do or where you want to go before you actually meetup. Improvising an entire first date on the spot just comes off as lazy.

Linda: “This one guy showed up and I asked him ‘ok what are we doing?’ and he said ‘I don’t know what do you want to do?’. We ended up getting coffee.”

Me: “Did it get better?”

Linda: “Nope. It started awkward and ended awkward.”

➢ Why would anyone not think of something before hand? Why would you want this awkward “I don’t know, what do you want to do?” stand off? Just pick a relaxed restaurant or bar. Don’t overthink it.


Rule 4: Do Not Go To The Movies

➢ A movie and dinner is probably the most stereotypical first date idea in existence, that doesn’t make it a good one. Besides lacking originality, it gives you relatively zero opportunity to get to know your date other than learning their favorite movie theatre snack (personally I like Milk Duds in popcorn just incase anyone cared).

Alison: “I hate movie dates. If a guy takes me to the movies for a first date I just assume he’s awkward.”

➢ I’d like to add that she did clarify movie dates can be acceptable if previously discussed. Meaning if she specifically says “I want to go see Wonder Woman” you should take her to go see Wonder Woman.

➢ If no good options come to mind take a look at some of our date bar choices.



Rule 5: Give Specific Compliments

➢ If you’re thinking “ok I’ll say I like her smile or laugh” you my friend are mistaken. She's (or he's that's your business) probably gone on dates before, meaning she's heard of the basic, cookie cutter compliments before. The difference is you have the dating rules for men to help you. You like this person enough to ask them out, think of something unique to them. I believe in you.

Maria: “Ughhh when a guy gives generic compliments like ‘I like your laugh’. It’s like ok what do you like about it or did you think of that before the date even started? It makes them sound like a kindergartner”

➢ Flex that vocabulary, especially with Maria. She’s a savage.


Dating Rules For Men Debate: Coffee or Drinks

➢ Coffee or drinks both make for pretty safe first date ideas. Both are relaxed, comfortable, low pressure dates, but which is preferred amongst our ladies?

Coffee: 4 - Drinks: 2

coffeePro coffee: “Coffee shops have softer music, the vibe is more relaxing so there’s less external pressure. But if you take me to a starbucks you’re done”

Pro Drinks: “I feel like I can be loose and open up more at a bar. I don’t know I feel like I’m more comfortable with a drink. It has more to do with me rather than the guy. It also gives me a chance to be cute wear a nice top or something, which is more exciting for me.”

➢ So this one really depends on the girl. Coffee appears to be the favorite amongst our opinion makers, but both are viable options.

Have any other dating rules for men you'd like to pass along? Make sure to comment below and help your fellow man!