11 First Date Tips for Men in Their Twenties

first date questions texting

First dates can be a lot of fun if you know what you’re doing. Men in their twenties won’t have any first date struggles if they just use these eleven tips.


It’s time to talk what to do on first dates. In my last letter I told you about all the classic mistakes most men make that you should avoid. A lot of misinformation pushes men to do WAY more than they should for a first date. As a result, a lot of guys are coming off as creepy and desperate instead of romantic and charming. Not you, my friend. I am going to show you that first dates are BASIC. Keeping it simple is the most efficient AND effective start to a relationship with a quality girl who is a great fit for you.

Setting the Date

Let’s start from the very beginning. You ask for a girl’s number. When you ask for her number you should name a time and place, and also give her a reason to go on a date with you. Example:

“It’s been great talking. Not many people share my sense of humor like you do. I’d like to hang out. Let’s grab drinks at Mike’s Pub. Are you free Tuesday? What’s your number?”

Don’t complicate it. As a matter of fact, the more infant your thoughts and words, the more authentic they come out.

Pre Date – To Text or Not to Text?

You have the date. You’re in good shape so far. A lot of guys try to continue the conversation via text so the girl “doesn’t forget about them.” I don’t think that is really necessary.

I think it is actually harmful, especially if you’re anything like me. Let me explain.

I’m not a great texter. My humor is far too dry and sarcastic for texts. Frankly, I come off as a total asshole when I text because I DO NOT play the “be funny and witty” games.

So what should you do? Keep it super simple.

Ask her out. Get the number. You can do it in person or ask her out on Tinder.

If you ask her in person for her number, afterwards text her something basic. “Hey Jessica, it’s James. Looking forward to drinks at Mike’s Tuesday.” You’ve covered all your bases with that super simple text. She now has your number, knows who the number belongs to, and a reminder of the date place and day.

If the girl is super interested she will sometimes take the initiative to try and start conversations with you before the date.

You can text to confirm the date on the day of or day before, but there’s no need to go much beyond that before your first date.

Just let your charm show in person. That’s what the date is for.

Once you have a good relationship going with a girl and she understands your humor, then you can joke more via texts. Until then, trying to be clever via text is a risk that bears ZERO rewards.

Key Takeaways

Should you text her a bunch before the date?

What’s the point? You already have the date. It’s yours to lose. There is no bonus from texting. Only chances for misinterpretations.

The Date Venue

Preferably, your first date venue will be a casual bar.

Ideally, you should make the first date all about you and go somewhere you love. Still, I want to give some very helpful tips.

The date venue should be somewhere you can interact.

  • Don’t go somewhere loud or crowded.
  • Don’t go somewhere you could get separated.

A moderately populated bar is a great place for a first date. There are just enough people for background noise and people watching. Usually there is a TV on.

Let’s pause right there to talk about TVs for a second, because they can be an asset.

Using TVs For Conversation

Commercials are just conversation starters cycled over and over. Don’t pay attention to the main programming (which is usually sports if you’re at a bar).

You can make fun of crappy commercials. Poke fun at infomercials. Think about if a shake weight commercial came on. What a jackpot!

Talk about the actual product advertised. Like, if you want the product. If you would use it. How you would use it. Your answers will be unique and personal, plus they invite her to contribute her ideas to the conversation. It’s a great way to get to know each other.

Need More Details On This Topic?

Where to Sit

Where you sit on your date matters big time. I’ve written about this in both Hang-Ups and Hangovers (it comes up on the date with Alexis) AND Redheads and Bedspreads (comes up on the date with Alesha).

I suggest a quiet bar for your venue because it’s a great place to chat. Furthermore, I recommend sitting at an ACTUAL bar. Not a table. AT THE BAR.

Why a bar? Good question.

I can answer that question first by explaining why NOT a table. A table creates a GIANT obstruction between you and your date. Also, a table has you both awkwardly facing directly at each other. Facing someone square puts on pressure. It can be uncomfortable and intimidating if your date is already nervous.

Why A Bar

When you are sitting at bar stools, it’s okay to face straight forward. There is a lot of pressure when someone is facing you square. It’s intimidating to some people. If you both are shoulder to shoulder and facing forward, she can feel more at ease.

Since it’s a bar stool, she has the freedom to turn her body toward you. When you pick up on that, you just turn your body toward hers to mirror her. Some girls take longer than others to warm up to you. Some may sit down and face you and put her feet on your stool and bump your knees. Some may spend 70% of the date facing forward.

Quiet Bars Make the best first dates

Quiet bars make for the best first dates.

Sitting in bar stools closes the gap between your two bodies, and opens the opportunity for touch. Girls are really great at sending signals with touch. Give her that opportunity.

The arm slap is a great one. Tell a funny joke, arm slap. Make fun of someone else at the bar, arm slap. Make fun of her, arm slap.

While you guys are talking she may touch you for no reason whatsoever. This is a great sign.

She can do this by reaching out and touching your arm or elbow with her fingertips while she talks. She might grab your wrist when she gets excited about a story she’s telling.

NONE of this is even POSSIBLE sitting across from each other at a table.

Think of all the great signals you’d be missing out on!

You can reach out and touch her as well. This is great for polarizing her.

After you guys have been talking for awhile, its super easy to just reach out and touch her knee. If she flinches, you’re not in great shape. If she doesn’t move, you’re good.

BONUS: Your touch might be the sign SHE has been waiting for. Remember, she is probably a bit nervous too. If you can let her know you like her with a casual touch, she might relax and cozy up to you.

Key Takeaways

Sitting at the bar (instead of a table) allows you to sit near each other without the pressures of facing each other.

It also affords you opportunities to touch (and even kiss).

Dating is About Patience

Like I said in my last letter, dating is all about patience.

As you go on more and more dates and practice how to touch women, your world and eyes will open up.

You’ll see all different reactions. You’ll notice her lean in. You’ll notice how she goes out of her way to touch you.

You’ll both turn toward each other. Maybe one of your knees will rest in between hers. Your faces just inches away while you talk.

You’ll get a first kiss sitting right there in your bar stools. There is just so much joy and fun in dating, if you just get out there and get as many dates as possible.

Accumulating these experiences will bolster your confidence. Ultimately, you’ll be surprised that very few girls flinch or draw back from your advances. After all, they drove all the way out to meet you. You should assume they like you to some degree.

How Long Should the First Date Last?

Easy. Two hours or three drinks. (Add 30 minutes or so if you venue change)

Some dates will go over. Some dates will even go under if the girl is just terrible (think Elizabeth from Redheads and Bedspreads). But the best rule of thumb is two hours or three drinks. Remember from our last letter that the NUMBER of interactions is what matters most, not the duration or quality.

If you are one of those guys who wants to keep a running score, points are only awarded for number of interactions.

When hanging out with a total stranger, there is a great deal of pressure and it can be exhausting for some people. So give each other a break after 2 hours.

Also, if the date is just going fantastic, it’s even better to bail at the two hour mark. It will leave her with a great impression of you and positive memories of your date. So quit while you’re ahead.

Closing the Date

As two hours approaches or you are finishing your third drink, ask for the bill.

If she offers to go halfsies, refuse. It’s a test.

My dating my not be traditional but I am a traditional type of guy. I believe in gender roles. I think the man should take the lead and handle the bill. Another reason to close the date at three drinks max: Many more and it gets expensive.

That being said, I have had girls handle the entire bill before (and then some).

In Redheads and Bedspreads, Kristina took the entire bill and then moved the date to another bar and handled that bill too (this date was a giant exception to the three drinks two hours rule). If a girl is that gung ho about hanging out with you, that’s an amazing sign. Let her do it. I’ll explain why.

Remember in my last letter I talked about cognitive dissonance? There are psychology studies that show when someone does you a favor, they like YOU more. The opposite is true if you do THEM a favor.

If you do someone else a favor, they feel in debt to you and they don’t like that. If they do YOU a favor, they resolve any dissonance in their subconscious by convincing themselves of how much they like you.

Key Takeaways

As a rule, the man handles the bill, unless she absolutely insists you split it (or she insists on paying for everything).

Leaving the Bar

When you receive the bill and decide how to pay it’s time to make (potentially) the last decision of the night.

  • Say goodnight
  • Invite her home

If you want to invite her home, the time to do it is while you still have the bill. You don’t want to spring it on her after you get up.

Should you invite her home? I would say yes.

If you don’t care about her, invite her home so you can at least get some action.

If you do care about her, see if she will tell you no.

Personally, when a girl would come home and hookup (sometimes within hours of meeting me), something inside of me would trigger and I just couldn’t respect that girl anymore.

I know, I was just as guilty as her. It’s a double standard, whatever. I can’t help it. It’s involuntary.

I just can’t imagine dedicating myself to that girl if she comes home and puts out on the first date. I’ll probably text her again at some late hour and say something like: “come over.”

Therefore, I would recommend inviting her home the majority of the time. As a test. Women test men ALL THE TIME. Why can’t we have ONE test of our own?

How to Invite Her Home

If you take ANYTHING from my books it should be the following infamous, date-closing line:

“I live like two blocks away if you want to hang out for a couple minutes.”

It’s almost a joke how many times this line gets thrown around in my books. Even when it didn’t make sense. Didn’t matter if it’s two blocks or three miles (it was always three or more miles).

This line is foolproof and I used to drop it no matter where on God’s green earth I was.

She’ll say yes or she’ll say “not tonight.” Either way, NOT A BIG DEAL. Either way, you DO NOT try to convince her to come over if she doesn’t want to. Have dignity.

Let’s say she agrees to come home with you.

Because you both should drive separate to the date, you just say: “Great, just follow me.”

Don’t offer her GPS or your address. When she sees it’s actually three miles instead of two blocks, you’ve created a hurdle for yourself.

I know this seems a little…sly. But it’s not. Hear me out.

If she has answered that she wants to go to your house, then she WANTS to go to your house.

If it’s a little farther away than two blocks that should be irrelevant. (If you are really far from home you may change the line from “couple blocks” to “couple miles” or “couple minutes.” Something like that).

One other thing I would do frequently is give a reason. “I only live a couple blocks away and the drinks are free at my house if you want to hang out for a couple minutes.”

Key Takeaways

It makes the most sense to invite her home the majority of the time. Don’t oversell it. Don’t give too many details. Just ask and be cool.

Go On Some First Dates

Having read all this, wouldn’t you agree that a first date is actually pretty simple?

Can’t you see how much fun spending a couple hours sitting with a beautiful girl at the bar would be?

So what’s your next step? That’s right, get as many dates as possible as quickly as possible.

I’m excited to hear about your experiences, my friend.

Good Luck,


P.S. A lot of the classic sales tactics I use come from sales books like Zig Ziglar’s Selling 101. It’s a short and tiny (and cheap) book with great tips for winning people over and closing deals!

About the Author Kyle Milligan

I'm Kyle Milligan, I write New Adult Books that don't suck. i.e. The Hang-Ups and Hangovers series. I like to write about the challenges of being a single twenty-something in today's hookup culture. My blog offers Dating Advice For Men.

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