Dating

He Says/She Says: How to Have a First Date That Isn't Awkward

Congratulations! You’ve made it to the first date, ladies and gents. Well done.

This is fun and exciting, but you may be feeling lots of different things at this point. You might have expectations, or you’re just trying to figure out what to expect. 

With so many thoughts and emotions running through your head now, there are a few simple things we’d like you to keep in mind as you approach your first date.

 

He says…

One word: casual.

Too many men make a crippling mistake in their dating life: In an effort to impress their lady, they overdo the first date.

But ultra-fancy, romantic, over-the-top first dates tend to have the opposite impact. Women perceive us as being way too serious and way too invested, and this scares them off. 

You are not going to impress her with expensive meals, fancy clothes or exotic locations. 

You know what will impress her? Showing her you know how to have a conversation.

My recommendation: Take her to coffee. Simple. Casual. Non-threatening. Want to add some kick to the mix and show her you’re not a generic Starbucks type of guy? Find a quaint, local place. She’ll love it.

During the date, ask her questions. Listen more than you talk. When she mentions her hobbies, take note; find common interests. If she mentions things like running, sightseeing, exploring museums, etc., this is pure gold: it’s perfect second-date material.

Now, this next thing should go without saying, gentlemen: Pay for the date. No exceptions. If she offers to split it, just smile politely, say “I’ve got this one,” and hand the cashier your payment.

At the end of the date, give her a hug (not a kiss) and thank her for spending time with you. 

But — and this is a big but, gents — don’t ask for a second date quite yet. She may not know how she feels yet, and she may feel caught off guard if you ask right away. Take two to three days to process, and allow her to do the same. If you’re still feeling it at that point, call her up and ask her out on date number two!  

 

She says… 

Three words: Just. Have. Fun.

This date is just an opportunity to get to know someone better. You don’t have to figure out how you feel about him. If you already know you’re interested in him, great! Just take it one step at a time and don’t freak out.

Let the momentum build based on his reciprocating interest. Both the guy and gal should be showing interest for things to move forward. 

Be gracious. You can offer to pay once at most, but let him be the gentleman and don’t fight it if he pays for the date. On that note, don’t have an entitled attitude about being paid for. Maybe offer to pay for yourself if things progress in the future. 

Say thank you for the date! Remember, he asked you out — and in guy world, that’s putting his ego on the line for you. It means a lot that he asked, so be sure to thank him.

If he doesn’t ask you on a second date right away, don’t be discouraged. Take the time to process how you feel, and let him do that as well. If he does ask you out again and you’re not interested, then be clear and thank him for taking the opportunity to get to know you, and vice versa. 

Also — and this is huge, ladies — don’t tell everyone about it. Or worse, put it on social media. Give things the privacy it needs to develop; then, maybe after a few dates and things are progressing, you can tell your closest girlfriends. (Just don’t tell 20 of them…) 

 

Bottom line: the first date should be stress-free, casual and fun. Just enjoy yourselves and see it as an opportunity to get to know another person! 

Next week, we’ll talk about what happens post first date — i.e., the awkward two-to-five-dates range before you talk about where you’re heading.




 Check out the rest of our dating series!

1. He Says/She Says: Your Utility Belt for Surviving the "Dating Apocalypse"

2. He Says/She Says: The Unspeakable "F Word" of Dating

3. He Says/She Says: How to Ask Somebody on a Date (and How to Respond)

4. He Says/She Says: How to Have a First Date that Rocks (and Isn't Awkward)

5. He Says/She Says: So You've Been on a Couple Dates...Now What?

6. He Says/She Says: The Virtuous Relationship

7. He Says/She Says: How to Break Up (and Keep Some Semblance of Dignity)