8 Signs That Signify You’re On A Real Date

We have discussed on multiple occasions the effects that the hookup culture is having on dating and courtship – primarily negative ones. When it comes to actually dating, people seem to be lost. We hear very little about people [Looking at you, men] putting in the time and effort to plan a real date as a sign of interest in a woman.

It has almost gotten so off track that we don’t even know what a ‘real date’ even looks like anymore, if we did want to plan one. For that reason, here are some pieces of the puzzle that have to be present in order to call it that. Otherwise you’re just hanging out.


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.

If you are not willing to put in the required effort to pick her up – maybe you don’t like her enough to be going out with her. Don’t have a car? Send one to pick her up – I bet no guy has done that for her before. Click here to get $20 off of your first Uber ride [See, you’re romantic and smart].

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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18 thoughts on “8 Signs That Signify You’re On A Real Date

  1. Love it but have to disagree with one thing… for safety reasons, I don’t give out my address early and would rather drive to and from the date alone for at least a while until I feel it’s safe to share that information. Later on, sure, I’ll enjoy being picked up and taken home but not until I feel it’s safe.

    1. I would be tempted to say that if a man has not successfully made you feel safe enough to pick you up then perhaps he isn’t the right type of man to go out with in the first place – but yes I completely agree with you and do sometimes make that statement in other articles.

    2. I agree with taking separate transportation to the date, especially if it’s a first date! It’s not just a safety issue, though that’s paramount. Like another commenter said, if you meet online, you often don’t know enough about a man to know if you are truly safe with him. When on a first date, you DON’T KNOW that it will go well, and it’s nice to be able to leave on your own accord if things go south. It certainly beats an awkward ride home with a man you barely know (who now knows your address, too!). Yes, it would be great to only go on dates with a man you feel you can trust, but with so much online communication that’s not face-to-face, you really don’t know who you are truly meeting.

  2. Side note to your “The man picks the woman up”- as a woman on a first date with someone way new (as in we didn’t meet through mutual friends, or he’s asked me out after a first meeting on the dance floor at a night club), for safety reasons, I’ll offer to meet the guy there rather than give him my home address.

    Along those same lines, if he tells me to call him when I get home, or he calls me to make sure I made it back safely (to address your last point), then I tend to think he’s interested and a potential good guy.

    1. As I have never had a woman request this it makes me wonder if men are failing to build enough trust before they ask a woman out. I understand the world is a dangerous place but I have personally never faced this objection.

      1. I think it happens a lot nowadays because of online dating. When you meet someone online, even if you talk for a while before that first date, those conversations cannot replace the gut feelings you get about someone when you meet them in person. Someone may seem wonderful online or on the phone, but when you meet them in person, something just isn’t right, and you don’t feel completely comfortable. And in those situations, a woman is happy she provided her own transportation for the evening.

  3. James, I applaud this wonderful blog message—and am taken aback that adults over the age of 21 have to be told what a date is—like we used to teach 16 year olds a generation ago. Can’t get over the term “online dating”—folks, the concept that typing statements back and forth with a stranger on a computer constitutes a “date” is just ludicrous. And the thought that anyone would go out on a formal date with someone they had never met face to face is just mind-boggling. You can’t start at Step 3. Step 1 is meeting the other person—in person. Building a person-to-person relationship is Step 2. THEN, deciding if you want to go out on a formal date, which would be Step 3. Yikes! Generation Y will really scare me if they then progress to “on-line marriages”–complete with children—never having made personal contact with the other people. Where are we headed when fantasies replace reality?

  4. Anyone have ideas on how some of these things may apply differently to college students where one or both people live in resident halls?

  5. I am in 100% agreement with the man picking up the tab. But the problem I am constantly having with my girlfriend is that she wants to pay it. Her excuse is since I only see her every 6 months that she wants to treat me at the date. I disagree. And it’s a hassle after that… What would you recommend?

  6. Great piece as usual but I disagree with what you said about the man not being the right person if he didn’t pique your interest enough to make you stop browsing on Facebook. The problem is certain people are addicted to Facebook or social media to a fault. They put it before a lot of things and if the man is to blame or seen as the wrong man for this act of cyber addictive ness on the part of the girl, that wouldn’t be a very fair thing to do, James.

    1. True. It could also be because the girl naturally has short attention span and like you said, cyber addiction. I have a girl friend who can never put her phone down despite a party being fun or when I talk during coffee dates.

  7. To Chris: Ask her on a date and meet her at her dorm and take her to a campus play or recital. Does she like basketball? Maybe there’s a museum at the school?

    Nic: Maybe send her a gift card the price of the meal as a “thinking about you” that way she gets her money back and u feel better.

    Stefan: if a person’s addiction over powers them to that extent then they shouldn’t date. I certainly wouldn’t want to be on a date w a person who had to stop and sniff cocaine every 30 minutes.

  8. James, I really enjoyed this article. But as a young woman who takes romantic relationships seriously, I personly balk at the idea of kissing for at least the first several dates. I’d rather know this could realistically be moving towards a significant relationship between the two of us before sharing something that personal and intimate.

    But I’m curious as to your thoughts, since you bring to bear a different perspective as well as a male one. 🙂

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