The 8-Point Checklist to Identify a “Real Date”


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One of the more common discussions I see happening regarding dating and relationships these days, is about the lack of actual dating that seems to be happening. Last minute texts to ‘hang out’ or invitations to ‘grab a drink’ seem to suffice.

That being said, there is a time and place for everything. Sometimes the more casual rendezvous is appropriate, but the way I see it, the amount of effort a man puts into planning a date is in direct proportion to his interest in the woman he is courting.


Unfortunately, as more casual advances become accepted more often, less and less effort seems to come forth – because why would it? Our generations are almost losing track of what a real date looks like, but my belief is that if you want to build a genuine, lasting relationship with someone – you’ve got to show that you’re willing to do so.

You actually identify it as a date.

This is so basic that I don’t even want to say it, but in today’s day and age I have to. Meeting up for a drink is not a date. Grabbing a coffee is not a date. A last minute text inviting her to join you out with your group of friends is not a date. Using the actual word and properly inviting a woman on a date is the first step to actually making it one.

The man picks the woman up.

I will never understand the ‘want to meet me there?’ mindset. If I am going to have enough interest in a woman to invite her on a date, you better damn well believe I am going to drive to her place to pick her up. If you are going to dinner and she is ‘out of the way,’ either find somewhere within reasonable driving distance of her place or be prepared to do the driving necessary to go to her place, the restaurant, back to her place, and then home again.

That being said, in the world of online dating and random connections, often times a woman may not be comfortable giving you her address unless you have built adequate trust already. The important thing is that you offer, and if she prefers to meet you there, don’t fight her on it.

There is an actual structure to the evening.

You certainly don’t need to spend hundreds of dollars, nor do you need to have multiple events planned through the night. The idea here is to actually put some thought into the experience the two of you are going to share. If you’re going to dinner for example, don’t just show up at a restaurant and hope to get a table. Find out what type of food she likes, make a reservation, ask for a nice table, and do it right.

Regardless of what your plan is, there should, in fact, be a plan.

You both actually care what you look like.

A date is no time for careless outfits. Taking the time to pull yourself together and put some real effort into your appearance shows both respect for yourself, and the person you are out with. Saying ‘this is who I am, take it or leave it’ is a great way to never get a second date.

Not to mention, we should want to look good for this person whether it is our first date or 100th date. The second we stop trying for them is the second things start to go south. If we start off that way, it’s safe to say you are doomed from the start.


The guy picks up the tab.

When friends go out, they split the bill. When you are on a date, the man picks up the tab. All of it. There are plenty of ways a woman can reciprocate if she’d like – she can take care of parking, pick up a round of drinks, get the snacks at the show you got tickets for, whatever it may be – but when the tab comes for dinner, don’t let her anywhere near it [and do not accept her offer to split it]. If you think paying for the date is about the money, think again.

You stay off your phones.

If the person you’re out with doesn’t keep your attention enough to make you forget all about your Facebook notifications for a couple of hours, then you’re out with the wrong person.

There is some sort of chivalry involved.

Whether it be opening doors, pulling out chairs, or any other small acts of kindness that signify romantic interest in a woman, these are small actions that show her you are actually interested in her enough to put in extra effort for her.

You get her home safe.

No, she probably doesn’t need you to escort her home. Yes, she has lived this long just fine without you by her side. But neither of those things mean that you should just part ways as the night winds down. You picked her up [right?] and should subsequently make sure she gets home safe as well.

Whether you are walking, driving, or taking a cab – it is imperative to end the evening on a positive note. Things can get dangerous at night for both men and women, and making sure she gets to her door will let her know that you care and are there for her, especially if she lives alone and/or in a city.


One last thing that I personally think should always happen on a date, but I won’t put it as a point because it is often contested, is a kiss. I believe if a man intends on pursuing a woman romantically, he needs to make it clear to her so that she doesn’t get the wrong idea and think he is uninterested. He should, of course, always be respectful and be confident that she is interested in return before making the move. But if the signs are there, the move should be made.

I also don’t believe one has to wait until the end of the night for a kiss. If things are going great, the attraction is there, and the opportunity presents itself – go for it.

So gentlemen – it’s time we show the women of the world that we still have it in us to build real, meaningful relationships. That we are willing to put in the effort to do more than just ‘hang out.’ Put the video games down – man up, suit up, and wine and dine a beautiful woman.


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  1. Krissa on April 18, 2016 at 1:01 pm

    Aww, Jeez – can we make this required reading for every hetero fella? Time for a revival of courtship! This is how you date like a grown man 🙂

    • Bea on April 27, 2016 at 9:18 am

      I totally agree 😊

  2. Barry on April 18, 2016 at 4:52 pm

    James, my mother would say a man that uses the word “damn” is not a gentleman. And she is Miss Manners to the T. Ladies: There are plenty of ways a woman can reciprocate if she’d like… Do you think any woman really wants to part with her shoe allowance? I love how women are so quick to point out how they don’t like stingy men, but always manage to look lost when any bill, no matter how small, arrives.

  3. Jay Colby on April 19, 2016 at 7:43 am

    Great post!

  4. Shannon Soper on June 4, 2016 at 5:32 am

    Really funny–I just got back from a sort of date-like thing, and felt a little confused, and found this article. Thanks for standing up for standards of respect and gentlemanly behavior!

  5. André Nickell on August 10, 2017 at 6:17 pm

    “She wants to be swept off of her feet, to be romanced, to be valued and appreciated” Same applies to men. And by the way, in my neck of the woods–Quebec– half the women think–and say– that they are to different degrees indulted when a fellah offers to pay…with responses like “you cant buy me by paying for my meal.

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