5 Simple First Date Ideas

Student: “Hey Rob, I managed to get a date with a girl I just met at Whole Foods the other day! I’m excited but I’m also incredibly nervous about what we should do on our first date together.”

Rob: “For the love of God, please tell me you didn’t suggest anything yet or do the cliche dinner or movie suggestion?”

Student: “No, is that what I should do?”

Rob: “…We’ve got more work to do, HAVE YOU NOT BEEN PAYING ATTENTION IN CLASS!?!?!?!?”

This was a question I got from a Dating Mastery Program student that I worked with a few weeks ago. Along with dealing with approach anxiety, this is usually one of the most common questions I get.

For the dating novice, after she agrees to meet up and hang out with you, this probably leads to the question, “So, what do I do now? How can I make sure this is a good date and not fuck up my chances with her?”

We’ve all seen this cliche trope play out in the movies and TV shows. The guy gets incredibly excited and starts brainstorming ideas for the perfect date. It’s usually followed by a ridiculous and funny fantasy that features a fancy dinner on top of the Empire State Building with fireworks, a violinist, wine, and Great Gatsby like attire, with the girl falling madly in love with him at the end of the date. Then it cuts back to his panicked state and the rest of the show is centered on him trying to nurture and create the perfect date that’ll either end in romantic sex or a complete disaster.

Fortunately for you, you don’t have to do this or go through the trouble of dealing with thousands of running gags other than me nagging you for the better as your conscience.

So to answer your question, what should you do?

Are you ready? This answer is going to be so mind-boggling that you’ll be shitting out gold…

As I always say, K-I-S-S. No, don’t make out with her yet, just KEEP IT SIMPLE STUPID!

Why You Should Keep Dates Simple

Society has both men and women conditioned to believe that first dates are supposed to be a formal and special event like graduation or going to prom or getting engaged. The reality of this is that it sets up both men and women to feel unnecessary and unrealistic pressure. I oftentimes don’t even like using the word “date” because it puts so much pressure on the girl and will set up a certain expectation for herself and for me to deliver.

The goal isn’t to blow her away with an amazing date idea. You’re not trying to get her to go out with you for the idea itself; you’re trying to get her to hang out with you for you. Your primary goal is to have a genuine connection with her, which could possibly lead to sex, and eventually the beginnings of a fulfilling relationship if both of you have good chemistry.

So besides the unnecessary pressure why should you keep dates simple, cheap, and spontaneous?

Expensive dates are a bad idea.

I’m not a cheapskate, but I will tell you one thing: YOU SHOULD NEVER EVER BUY A GIRL’S LOVE, PERIOD! Between the awkwardness of how to split the bill, the dent in your wallet, and the fact that you’re investing so much money in a girl you don’t even know yet, it’s just not worth it.

It doesn’t matter if you’re financially well off or rich, it’s not going to bode well for you. If she’s not a gold digger, she’ll probably end up feeling bad or feeling like you’re trying to buy her affection, and will make her feel like or paint her as an object or prize. It’s unnecessary pressure. Expensive dinner dates are something you do on your anniversary with your girlfriend or wife, not on first dates.

Complex dates are a bad idea.

As a man, it’s your responsibility to lead. Making everything complicated will make her less likely to want to invest in you. Plus, complicated date ideas come with complicated logistics. Just remember that besides the stuff you have going on in your life, she has a life too.

Complex dates get in the way of connecting with her and leading her. What it will do is send you to the friend zone. For the sake of simplicity, avoid making things complicated for you and her. You can do that stuff after you’ve slept with her and have been dating her for a while.

Cheap and simple dates make everything easier for you to connect with her, lead her, and make things sexual.

If you didn’t heed my advice or already landed in the dreaded friend zone, please refer to this article on how to get out of the friend zone.

The Solution

There are thousands of simple first date ideas, but I want you to re-frame and change your paradigm or idea of what a date looks like or what it should be. Emotions are contagious, so if you’re nervous, imagine how she’s going to feel or is probably feeling about going out to do something with a complete stranger she just met.

Re-frame this in your mind and hers when you communicate and set up the logistics for the date. You’re hanging out, that’s it. Just like what you do with your buddies, your family, and your co-workers when you go on your lunch break, you’re simply hanging out.

So imagine how you hang out with your best friend or your buddies. That’s what you’re going to do with her on your first date. With that, let’s get on to five simple (and affordable) first date ideas.

Simple and Affordable First Date Ideas

1. The Coffee Date

As cliche as this may sound, it doesn’t need to be coffee. It can be pastries, bubble tea, donuts, or croissants. It’s incredibly low pressure, intimate, and cafes are everywhere and usually within close proximity to a park or smack dab in the middle of a city or town square where there’s plenty of places to walk and talk. If you’re not into the walking and talking aspect, you can just sit in the lounge area couches or the bar area if it’s one of those espresso bars.

I don’t recommend tables because it’ll create a barrier. I recommend you find a couch to sit on, or go into the park and sit on a park bench with her. This will make touching and getting intimate with her much easier.

2. The Happy Hour Date

Since my college days ended and I’ve recommitted myself to my health and fitness, I don’t really like going to bars to drink. At this point, when I do drink, it’s not to get loaded, but more just to unwind and relax after a long day.

But when I was in college, this was my go to option because the bar is a social environment and it’s low pressure. Unlike taking her out to a fancy dinner, where you’re forced to commit to a 1-3 hour ordeal with someone you know nothing about, going to a bar during happy hour is much more casual.

If you don’t vibe well with her or if she doesn’t vibe well with you, you can leave after the first drink. You also have the benefit of being able to bounce around, like getting coffee with her during the daytime. You can also go to another bar down the street and have a little mini adventure.

Here are some more tips for having a great happy hour date:

Keep it moving.

Try not to get more than one round of drinks at the same spot. This is simply meant to prevent the date from getting stagnant. You can either switch bars, have a round of drinks by the pool table or lounge section, or just move to another place with good happy hour deals.

Give and take.

A lot of guys over complicate the process of paying the bill. When it comes, just say you’ll get the first round and she’ll handle the next. 9 times out of 10, most women are cool with this, and only on very rare occasions they’ll get pissed.

I usually use this to screen out which girls I’m going to vibe well with. If she’s got good values and is just a cool person, then of course don’t be afraid to shell out some cash. But if she gets pissed over something like this on a first date, then it’s best to move on.

Sit next to her.

Just like the coffee date, sit next to her at the bar. The closer the proximity and the more touch, the easier it’ll be to build a romantic connection with her.

3. The On-the-Go Food Date

This one is my personal favorites, since I get to bring out my inner fat kid. If this is a daytime date, right after work, or even after an event or class where you just met her, I recommend just grabbing a slice of pizza, ice cream, hipster meatballs if you’re in Brooklyn, or frozen yogurt.

As a bonus tip, have a plan for what you’re going to do afterwards. These kinds of dates won’t take more than 10-20 minutes. I recommend walking to a nearby park, the pier if you live near one, or around the corner to your place if you live nearby. The point is, have a plan and don’t over-complicate it.

4. Running Errands Date

Now I know you’re thinking, “Why would I take her with me while I run errands?” Remember what I said about re-framing this as hanging out. I used to do this all the time when I was in college and still do as my primary means for going on dates, because I always have something on my schedule and scheduling dates is tough since my only “me time” is usually Sunday.

You can kill two birds with one stone. Go on a date and also get shit done. Usually I turn it into an adventure where we end up exploring as I pick up my laundry or go food shopping.

You don’t necessarily have to plan out a date. Just bring her along on something you were already doing. This saves time and doesn’t require any planning. For example, if you’re going food shopping you can say, “I’m heading over to Whole Foods to pick up some groceries, want to come with me and we can grab some food afterwards?”

Ironically and unintentionally, after doing this for a while I realized that it puts you in a position of higher value just because you’re not doing any selling or chasing. You’re just going on about your day-to-day life and taking her along for the ride.

This also takes off the unnecessary pressure that comes with going on a first date. You come off as down to earth with a normal life, which in turn will make her feel more comfortable with you. This leads to an easier time connecting with her and seducing her if you plan on having sex on the first date.

Some examples of running errands dates:

  • Walking through the city as you go to an appointment
  • Going to a networking event you originally planned on attending
  • Window shopping in the mall while you’re shopping for clothes
  • Going to a farmer’s market or flea market
  • Laying a blanket in the park and having a “spontaneous picnic” on your lunch break.

5. Hookah Bar Date

These days, unless it’s a special event, birthday, wedding, or holiday, I rarely ever drink since my re-commitment to health and fitness. But my occasional vice next to eating cheeseburgers and donuts is smoking hookah. There’s a number of reasons why I recommend taking her to a local hookah bar:

  • It’s intimate.
  • It’s loungey.
  • The light lounge music sets the mood.
  • The smell of flavored tobacco and hookah charcoal sets the vibe and in my opinion smells good.
  • It’s dim so it’s easier to sexually escalate.
  • It’s a great place to just relax and unwind after a work day or after class.
  • They serve good food.
  • The seats are usually designed like the lounge area in the bar where you can sit with her get more intimate.
  • It’s a fun atmosphere if there’s live music.
  • If they have karaoke then you can be silly and sing with her.
  • It’s quiet enough where you can have an intimate conversation.

So there you have it, five simple and affordable first dates. At this point, you’re probably asking if you should push forward and either bring her back to your place or go home with her. Every girl has a different threshold, but always make sure to test and see how she reacts.

A lot of times I’ll go home with her. If she’s the type who wants to take it easy, especially if she’s fresh off a break up, then I usually aim for the second date and at least try to kiss and make out with her once I get her in a private area. Don’t get me wrong, sex on a first date is very common if you’ve built enough comfort with her, lead her, and set up good logistics. The sooner you hook up, the better it’ll be for both you and her.

Why It’s Better to Hook Up Sooner Rather Than Later

Attraction has an expiration date.

This is why I make it a point to try and move things forward on the first date. If sex isn’t possible, just kiss her at least. Attraction doesn’t last forever, and once it fades, you’ve probably lost your at bat.

You discover if you have sexual chemistry sooner than later.

Some people have great chemistry off the bat, while other’s just don’t. What I’ve learned is that good conversational chemistry, a lot of flirting, and healthy emotional chemistry usually leads to good sex. Sometimes, these things just don’t fit well together, and the sooner you figure this out, the better it’ll be for both you and her.

You’re not going to the friend zone.

If you’ve made out with her or have made it to first, second, third base, and lastly home plate and you do it well, you’re not going to be condemned to the friend zone, unless you act crazy or needy afterwards.

Women are attracted to dominant men.

Dominant men go for exactly what they want. If you want to have sex with her and you don’t make the first few moves, you’ll lose respect and brownie points with her. If you still don’t know your “GO” signals, please refer to this article on the five signals she wants you to make a move.

Unique Situations

As I always say, every girl is different with a unique set of experiences and sometimes baggage. If you’ve gone on more than three dates with her and you still haven’t had sex or at least gone to first, second, or third base, then it most likely means one of the following:

  • You don’t know how to sexually escalate.
  • You didn’t take any of the advice above and suck at planning simple dates.
  • She has some reservations or issues about having sex.
  • She’s emotionally unstable or came off a really bad relationship (at this point, just save yourself the headache and walk away).
  • She comes from a conservative culture or is religious.
  • She’s still a virgin.

‘Til Next Time,


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Rob Virges

Hi, I'm Rob and welcome to our website!

In the last decade I've been coaching men (and women) in the art of connecting and finding love. I can tell you I've been referred to as "an asshole with a heart".

Just like other men who've been trying to figure out and understand the dating game, I used to be socially awkward. I'm a former Dating Mastery Program alumni and CofC apprentice with a decade worth of experience under my belt as a student, coach, and lifestyle mentor. My background is in applied psychology and I utilize a combination academic theory, research, and practical application towards our coaching.

I'm not a creepy pickup artist. I'm a normal guy that's competent, confident, and comfortable with women. My job is simple and that's to understand, nurture, support, motivate, and help you achieve and possibly realize the best version of yourself so you can authentically express yourself, connect with women (or men), and help you achieve whatever your dating goals may be in the most holistic, comprehensive, and practical manner.

Welcome to Craft of Charisma, The #1 company for teaching people to authentically connect, love, and nurture healthy relationships that can last a lifetime.

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