Why is This Here?

As a shy guy and an introvert, I may want to live alone in a cabin sipping Scotch by the fire, but I can’t deny the truth: human beings are social creatures. Knowing how to interact with people effectively will not only build your confidence, it will enrich your life.


first date tips for guysOne of the things that can make dating such an intimidating proposition for a lot of guys is that each step along the way presents its own unique set of challenges.

First you have to learn how to talk to a woman confidently enough to ask her out, and whether online or in person, that’s no small task for guys who find themselves on the shyer or more introverted end of the spectrum.

Then, once you’re lucky enough to secure the date, a whole new set of nerves kicks in. Where will you go? What will you talk about? Should you kiss her at the end? If so, how will you know? (Read on for much more on this.)

Just thinking about it is almost enough to make your palms sweat, to say nothing of your pits. (No? Just me? Well then, that was an embarrassing over-share…)

Firsthand Experience
(in f@¢&ing it all up)

Unfortunately, I know that nervous feeling all too well. I didn’t go on a lot of dates when I was in college, so when I moved to the city and started going on real, grown-up dates in my early 20s, I was basically terrified.

I had all of the above questions and concerns, plus about a hundred more, and my over-thinking made me feel anxious and out of sorts—and during the date, it showed.

As you can probably imagine, when you’re not very good at first dates, you don’t often get a second one—which means you really have no choice but to go back to the drawing board and try to find another first date. And another. And then another…

“Experience” Being the Operative Word

And while this can be both pretty disheartening and very expensive (the only thing worse than looking at my phone to see that she hadn’t responded to my texts was looking at my credit card bill a few weeks later), it does offer one silver lining:

All that first-date practice makes… well, if not perfect, definitely an improvement.

Eventually, I got good enough at first dates to secure a second. And then a third. And then a fourth, a fifth and, in due course, I even found myself with a loving (and amazing, and beautiful, and wonderful) girlfriend.*

first date tips for guys
Time travel doesn’t exist (yet), so I can’t share this with my younger self—but I CAN share it with you

Unfortunately, Doc Brown doesn’t really exist, and Elon Musk seems too obsessed with Hyperloops and solar roofs to focus on the truly important work of building a flux capacitor and perfecting time travel—all of which means I can’t go back in time to spare my younger self from his many (oh, so many) mistakes.

But I can share what I’ve learned here and provide some first date tips for guys (and particularly introverted or shyer guys like myself) who want to avoid my errors, rather than spend hundreds of dollars on bad dates learning how to correct them.

So without any further preamble, here are the first date tips I wish someone had told me when I first started dating.

*…who happens to read my blog.

first date tips for guys

First Date Tips for Guys

1. She’s Nervous Too

first date tips for guysThis is something that’s easy to forget, particularly for shy or introverted guys. When I was younger, I would get really nervous before a first date, and start obsessing over details: “What am I going to wear? What am I going to say? How am I going to act?”

The one thing I didn’t think much about? My date. And more specifically, what she might be thinking and feeling as she prepares for a first date.

Guys who feel nervous or even intimidated talking to women can often make the mistake of assuming that they’re the only ones who feel this way.

If we think about other people’s thoughts and feelings at all, it’s usually only briefly, because we assume that they’re much more comfortable with social interaction and we’re the ones who are at some kind of social deficit.

But the truth is that’s just our negativity bias getting the best of us. According to Psych Central, about half of all people consider themselves shy, meaning there’s a good chance that you’re not the only one feeling nervous about your date.

Recognizing that your date probably feels a lot of the same trepidation that you do has two big benefits. First, it makes you feel less like an outlier and more comfortable with the idea of meeting up with her—after all, at least you know you’ll have at least one thing in common.

Second, shifting your focus to her nerves helps keep you from obsessing about yours. Obsessing over the things that make us nervous tends to accentuate and highlight them in our minds, which only leads to more over-thinking. Focusing on something else – anything else – relieves us of this pressure.

First Date Tip #1:

Imagine that your date is really nervous—at least twice as nervous as you are. Instead of obsessing over what you’ll do to look and sound cool, think about ways you can make her feel comfortable instead.

This will shift your focus away from your own nerves, and even if she’s not quite as nervous as you imagine, she’ll appreciate your making an effort to make sure she’s comfortable.

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2. Compliments Show Confidence

first date tips for guysThis might seem a strange confession, but I have to admit that for a long time I felt kind of uncomfortable paying people compliments.

On the surface, this doesn’t make any sense: I know people like hearing nice things, and I want people to know when I admire something about them. But for years I found it difficult to actually spit out positive sentiments when I felt them.

Maybe my discomfort owed to my (woefully misbegotten) notion that I should play it cool at all times and not reveal what I was thinking or feeling to people. Or maybe it was just my general shyness kicking in, which often made it difficult to talk to people about anything.

I’m not sure where this strange fear came from, but when I read the book How to Win Friends & Influence People in my early 20s, I became very aware of just how much it had held me back.

In a section about becoming a friendlier person, author Dale Carnegie implores the reader to “give honest, sincere appreciation,” explaining:

“Nothing else so inspires and heartens people as words of appreciation. You and I may soon forget the words of encouragement and appreciation that we utter now, but the person to whom we have spoken them may treasure them and repeat them to themselves over a lifetime.”

A little heavy handed? Sure, just a touch. But is it accurate? Like Clint Barton at a shooting range.

Leaders Build People Up

first date tips for guysAfter learning this lesson from Carnegie’s book, I started paying more attention to when compliments are paid and who gives them, and I noticed something that now seems so obvious, I can’t believe I wasn’t aware of it before.

Generally speaking, the people who compliment others most often are those who have the most power (whether real or perceived). This makes sense too, since, as mentioned above, people who are shy, nervous or insecure generally tend to think more about themselves and their insecurities than other people.

But people who are comfortable and self-confident devote less mental energy to themselves and more to others, allowing them to not only notice others’ strengths, but also make sure people know they’ve been noticed.

No wonder Carnegie implores us to be “hearty in your approbation and lavish in your praise.”

A Quick Caveat

Before we move on, I just want to note the importance of two of Carnegie’s words: honest and sincere.

Paying people false praise will have the opposite effect of what you’re intending: it will make people suspicious of you, and with good reason. Most people have pretty well honed bullshit-detectors, and they can tell when someone’s just trying to butter them up. If they suspect that’s what you’re up to, they’re going to think you’re smarmy, not charming, and the whole endeavour will be for nought.

So make sure to keep your praise honest and sincere. But when praise is warranted, don’t hold back in expressing it.

Oh, And One More Thing…
first date tips for guys
“You’re so purty…”

Sincere compliments are great and can go a long way to making people feel comfortable around you, but be wary of too many compliments about her physical appearance.

Offering a sincere, “Wow, you look great” when the date starts is appropriate and will be appreciated. But beyond that, don’t overwhelm her with compliments about her body or her look. You don’t want her to feel objectified, or think that you’re only dating her because of her physical appearance. (You’re not, right?)

Instead, look for opportunities to praise her for who she is and what she does, not how she looks. When she tells you about what field she studies or works in, you can point out its challenges and say, “You must be really…” then fill in the blank with whatever traits are necessary for her field: smart, hard-working, patient, organized, etc.

Look for ways to compliment her on things other than her looks and she’ll recognize you as a man whose appreciation runs more than skin deep.

First Date Tip #2:

Compliment your date honestly and sincerely. Not only will it make her feel good (which, as noted in Tip #1, should be one of your goals), it will convey your confidence and bolster her perception of you.

3. Don’t Defer the Date Planning

first date tips for guys
“Just pick a time and place already…”

This is a mistake a lot of guys make when they first start dating, and it’s an understandable one.

After all, you want your date to think you’re nice, agreeable and kind, and there’s nothing wrong with that. The mistake is in going too far to demonstrate those traits, which often results in guys bending over backwards to avoid making any date-related decision unless they’ve solicited her full and robust feedback.

This manifests itself most often before the date has even begun. Once the date is agreed upon, someone has to pick a time, place and activity. It’s tempting to think that you should consult closely with her on this in order to choose a venue or activity that she’s going to enjoy.

But remember, you don’t know much about her yet, and teasing this information out before you’ve even gone on a first date is often more annoying than accommodating.

An (Agonizing) Example

first date tips for guysLet me give you an example. If you’re too focused on being accommodating, the first conversation you have about your date might go something like this:

Her: Sure, I’d love to go out with you.

You: Great, where do you want to go?

Her: Ummm, well I don’t know really, I’m up for anything.

You: Well, do you have any favorite places?

Her: I mean, I’m not sure, there are a lot of places I like…

You: OK, what are your top three?

Pause here and ask yourself: how did that read to you? Did it give you the impression that you were doing her a favor by being super accommodating, or did it feel more like you were shifting the burden of date planning over to her — and maybe even giving her the third degree about her interests?

A More Attractive Alternative

first date tips for guysLet’s take a look at how that conversation could go if you were just a little more decisive, while still being accommodating:

Her: Sure, I’d love to go out with you.

You: Great, I was thinking we could grab a drink at the pub on Main Street, do you know it?

Her: Oh, I don’t really like that pub actually, I’ve had really bad service there in the past.

You: Oh no problem, how about the wine bar on 4th street?

Her: OK sure, that sounds good.

In this example, you still come off as being accommodating – you’re not going to insist on going to a bar she doesn’t like – but you’ve also clearly put some thought into the date ahead of time and came to the table armed with some ideas.

Taking the reigns and doing this kind of advanced planning has a number of advantages. It suggests that you’re a go-getter who knows what he wants, that you’re not a hermit (because you’re familiar with the bar/social scene in your city), and most importantly, that you’re willing to take responsibility, rather than making her do it.

First Date Tip #3:

Don’t saddle your date with the responsibility of planning what you’ll do. Have a few options in mind and suggest your first choice. If she’s up for it, you’re all set. If not, be flexible and offer a back up, or adjust the plan as needed.

4. Conversation Comes Naturally
(No, really!)

One of the things that used to scare me most about dating was not just the fear of being rejected and failing to get the date in the first place (though there was a time when that fear was basically crippling).

Instead, what scared me most was trying to figure out what the hell we would talk about if she actually said yes.

I used to be terrified of, and consequently terrible at, making small talk, so the prospect of talking directly to an attractive stranger for hours on end was among the most intimidating propositions I could imagine.

But looking back on it now with the benefit of hindsight, I realize just how misplaced (and utterly unnecessary) that fear actually was. When two adults want to talk to each other, they’ll find something to talk about. Especially if they happen to be in a situation where they a) find each other attractive, and b) have enough in common that they agreed to go out with each other in the first place.

Studying the Art of Small Talk

Of course, I have to admit that my newfound conversational confidence isn’t entirely natural.

Once I recognized that my fear of making conversation was holding me back not just romantically, but socially and professionally as well, I decided I had to do something about it.

But being an introvert (and a self-avowed word nerd), I didn’t feel comfortable heading to the bar to randomly start chatting people up. So instead I headed to the bookstore.

I devoured books like How to Talk to Anyone, How to Win Friends & Influence People and The Charisma Myth, among (many) others, and learned that while some people may be natural talkers, the ability to make conversation isn’t some magical gift from the gods—it’s a skill.

And as with all skills, when you learn a few easy-to-implement tactics, you can get significantly better at starting conversations, keeping them going, and avoiding those dreaded awkward pauses that can stop a chat dead in its tracks.

To help you spark some fun, interesting and engaging conversation on your date, I’ve put together a list of 14 foolproof first date questions for my email subscribers, along with a few follow-ups for each. Just fill out the form below, and I’ll send you some surefire ways to keep the conversation flowing all night.

14 Foolproof First Date Questions
(Plus! 37 Follow-up Questions to Keep the Conversation Going)

Enter your email address below to get 14 fun conversation-starting first date questions sent straight to your inbox.

First Date Tip #4:

Don’t fret too much about what you’ll talk about on your date, because conversation comes more naturally than you might think. But if you don’t want to completely wing it, enter your email address in the form above and I’ll send you a list of questions that will make first date conversations a lot easier.

5. Ask Open-Ended Questions

If you don’t think that an animated eight-year-old has anything to teach you about dating, then you, my friend, have not seen enough classic episodes of The Simpsons.

Way back in a 1993 episode called “I Love Lisa” (sidebar: holy shit this show is old), Ralph Wiggum pursues Lisa Simpson after Lisa gives him a Valentine’s Day card out of kindness. Ralph finally gets what he wants when Lisa agrees to go out with him, but when the date begins Ralph finds himself tongue tied — and makes a classic conversational mistake:

“So, do you like… stuff?”

In addition to being hilariously asinine, Ralph’s question suffers from a key structural flaw: it’s a closed-ended question. By asking questions that begin with “Do you like…” you’re only leaving your date (or any other conversation partner, for that matter) two ways to answer: yes or no.

first date tips for guys
“Yeah buddy, I like stuff. Thanks for asking.”

The problem is that it’s hard to answer yes-or-no questions in a way that moves the conversation forward, even when your subject is a little more interesting than “stuff.”

For instance, let’s say you want to talk about movies. Movies can make a great small talk/first date topic because they’re so ubiquitous; everyone watches them sometimes and has their own favorite genres, films, actors, directors, etc.

But if you start the movie conversation with a straight yes-or-no question, you can stop it before it even gets rolling (and yes, that was a film pun).

You: So, do you like movies?

Her: Umm, no, I don’t watch a lot of movies.

You: Oh, uhhh, why not?

Her: I don’t know, I’m just not that into them.

Now you’re left two options, neither of them great: you can either try to force the movie conversation when she’s already declared a lack of interest, or you can pivot away from the topic immediately, which might make for an awkward transition.

first date tips for guys
Ask an open-ended question, get an open-ended answer

By contrast, when you wade into the topic with an open-ended question, the conversation can flow more naturally, whether she likes movies or not.

You: How do you feel about movies?

Her: Actually, I’m not a big fan.

You: Really? That’s interesting, why do you think that is?

Her: I’m not sure exactly. I was always a bookworm as a kid, so I think I just prefer…

By asking how she feels about the topic instead of “do you like…” you give her a chance to express something about herself, rather than just provide a minor detail about her preferences. This opens the door for all sorts of follow-up questions based on what she says, which is what really gets the conversation going.

First Date Tip #5:

Before your first date, think about a few interesting topics you want to raise, and give some thought to how you can ask about them with open-ended questions. In general, asking about what she thinks or feels (e.g. “What’s your take on…?” or “How do you feel about…?”) is more effective than questions that start with “Do you…?”

6. Do Your Homework

first date tips for guys
No, this DOES NOT mean cyber-stalk her. Keep reading to find out what it does mean.

One of the reasons talking to a stranger is so intimidating is because you really don’t know anything about them, and therefore don’t know what to talk about to get the ball rolling.

But if someone has agreed to go out on a date with you, she’s not really a stranger. Sure, you might not know much about her, but I bet you know where to look in order to find out more.

If you met her online, go back and re-read her profile before your date. What does she list as her interests? Does she make any jokes or offhand remarks you could ask her about or follow up on? What about her family, does she mention how many siblings she has or where she grew up?

If you met her through mutual friends, you can ask these kinds of questions of them to get the inside scoop (and since women tend to talk about this kind of stuff more than men, you can bet she’s probably doing the same).

Putting in this kind of legwork has two advantages. For one, it’ll give you even more conversational ammunition and help ensure you have plenty to talk about on your date. But even more importantly, it’ll show her that you’re really interested in her—her life, her hobbies and her thoughts/opinions.

Cite Your Sources
first date tips for guys
When asking about her, make sure she knows where you got your info.

One word of advice when referencing things from her life: when you bring it up in conversation, it’s a good idea to mention the source.

If you want to follow up on something she wrote on her profile, say “Your profile said you’ve been skydiving before, what was that experience like?” If you reached out to a mutual friend for some insight, say “Rob mentioned that you like horseback riding, how did you get into that?”

The sad truth is that in the digital age, everyone is at risk of being cyber-stalked, and while you and I may not worry much about this, women are much more sensitive to it.

Referencing your source shows that you’re interested enough to pay attention and take interest in her, but above-board (and sane) enough to keep your research well within the public domain.

First Date Tip #6:

Find out a few more specific things about her so that you can ask questions that go beyond the same rote “getting to know you” questions she’s been asked before. But remember that if you’re going to get a little more personal, you want to cite your sources so she knows that you’re interested, not creepy.

7. It’s Not Just About Getting to Know Each Other

first date tips for guysThis is a tip that my friend Rick over at Date School preaches:

“On a first date, fun trumps facts, hands down,” he writes.

I really wish I had learned that one a decade ago.

Back then, I tended to use the same template for every first date: pick a quiet bar, or quiet coffee shop, or quiet place to walk, where we could talk and get to know each other. Then, I’d ask biographical questions of the sort I suggested above ad nauseum, and find myself shocked when she would fail to respond to my texts after the date.

But while doing your homework and having a few good, pertinent questions in your quiver will definitely help show your date that you’ve taken an interest in her, that doesn’t mean the right move is to grill her on every aspect of her life story.

Don’t Forget the Fun

Generally speaking, it’s true that people love to talk about themselves, but they also like to have a good time—and they inevitably like people who can show them a good time.

“The purpose of any date, but especially a first date, is to have a fun first date,” Rick writes over on his Date School blog. “You need to have FUN with someone so you can truly see if you feel attracted to each other.”

first date tips for guysHe’s totally right. You can sit down and share a meal or a few drinks with someone and collect all sorts of data about them: where they grew up, how many siblings they have, what they studied in school, etc.

But attraction, romance and – dare I say it – even love are about so much more than that.

Some of the most cherished memories my girlfriend and I have are from trips we took or activities we did. The time we saw the Redwood trees in San Francisco. The epic bike ride we took in France. Helping her work up the courage to go down the waterslide at our hotel (then watching her go again, and again). These are the moments that really brought us together.

Give some thought to things you can do in your city that will create a memory – and a bond – she won’t soon forget.

First Date Tip #7:

Ask yourself: what are some things that tourists would do in your city? Think about fun things that involve getting up and moving a bit – bowling, axe throwing, even just going for a walk in the park – rather than just sitting in a movie theatre or bar.

8. Authenticity  Beats   Bravado

first date tips for guys
Spoiler alert: she doesn’t want two tickets to the gun show

There’s probably no scenario where you want to put your best face forward more than on a first date. After all, first impressions are powerful, and the old cliché about them happens to be true: you only get one chance.

But the mistake some guys make (and “some guys” is definitely a group that includes me) when they first start dating is to lay it on a little too thick. In an effort to come off as cool, interesting, intriguing or worthy, it’s tempting to look for ways to play up your best qualities.

This can manifest itself in a number of ways. Maybe you try to shoehorn the fact that you were valedictorian into the conversation to let her know you’re smart, or make a big deal out of picking a fancy venue to imply that you have money.

Either way, if you try to play up an attribute in a way that doesn’t feel authentic and organic to the situation, it’s going to have the opposite of your desired effect: instead of seeming cool and competent, you’re more likely to come off as shallow, petty or insecure.

first date tips for guys
“It was the funniest thing, I was out on my parents yacht— I mentioned my parents have a yacht, right?—so I’m out on the yacht, and…”

The same thing goes for exaggerating – or outright lying – to make yourself seem cooler. People can see through phoniness pretty easily, and women, in particular, tend to have pretty good bullshit detectors.

Even if you somehow (briefly) get away with it, there will eventually be a cost: at some point she’ll learn that you are not, in fact, a Nobel Prize-winning philanthropist/neurosurgeon, but you are a liar.

Instead of fudging the truth or bending over backwards to try and show your strengths, try coming up with date ideas that play to them naturally. If you’re a student of stand-up, take her to a comedy club. If you’re a pool shark, take her to a pool hall. If you’re a bowling fanatic, make better life choices take her to a bowling alley. Just remember not to be too competitive if you’re doing an activity where you’re experienced and she’s not.

And if for whatever reason you find yourself in a situation that you’re not naturally inclined towards, try admitting and acknowledging your flaws rather than trying to hide them. Owning up to your weaknesses is a sign of strength, and an attractive mark of self-confidence.

First Date Tip #8:

Authenticity is attractive. Do what you can to choose a venue and activity that will naturally play to your strengths and help show her who you are, but if your flaws do reveal themselves, don’t be afraid to acknowledge and take ownership of them.

9.  Skip  the  Kiss

first date tips for guysThis may be the most controversial point on this list, and I know not everyone will agree with it. But allow me to make the case for skipping the first date kiss altogether.

Just as you want to make a strong first impression, you also want to end on a high note. I recognize that for a lot of guys, that means finishing the date with a kiss – or more – and I can definitely understand the desire to get physical fast.

But foregoing the kiss on the first date has a number of advantages.

A) It Spares You Some Nerves

First and foremost, it alleviates you of a lot of anxiety. First dates can be nerve-wracking, and no moment more so than the end. As you attempt to keep up the conversation and maintain your composure, your mind races and your heart rate skyrockets as you frantically try to figure out where, when and how to lean in and go for the kiss.

But deciding from the outset that you’re going to skip the kiss and go for a hug at the end of the date completely frees you of all that stress. Instead of seeming nervous, fidgety and awkward as you desperately try to read the signs and strategize, you’ll be calm, cool and collected because you already know how the date will end—on your terms.

B) It Avoids Awkwardness

first date tips for guysSkipping the kiss doesn’t just help you avoid anxiety—it helps you both avoid some awkwardness.

Sometimes after a first date, it can be hard to tell if you should kiss each other or not. You start doing a kind of romantic calculus in your head like, “OK, she seemed to have a good time. I think she likes me. She might be giving me the sign. Wait, was that a sign? Or was she just scratching her ear? This is confusing.”

In the best case scenario, she’s thinking something similar and also doesn’t know how to initiate. In the worst case, she doesn’t want you to touch her and any attempt to put your lips on her will be wholly unwelcome.

Knowing from the start that you’re not going to kiss means that you’re also not going to bother doing that awkward dance. If all goes well, then she’ll likely want to see you again. And after a second date – and twice as much time spent getting to know each other – it’ll be much easier to infer that you like each other, and a lot less awkward when you kiss for the first time.

C) You (Might) Leave Her Wanting More

first date tips for guysSkipping the kiss and its ensuing anxiety may help you feel better at the end of the date, but what about her? I started this post by imploring you to think about her wants and needs, and if you guys hit it off and everything went well, she may be expecting you to pucker up before you part ways.

But holding back can actually pay dividends down the road. People naturally tend to want what they can’t have, which is why “playing hard to get” has been a dating strategy for about as long as dating’s been a thing.

If she wants to kiss you at the end of the first date, then it stands to reason that she’ll also want a second date. But by showing a little restraint and skipping the kiss the first time around, you’ll inject a little mystery into the equation, which will make her more curious—and eve more excited to see you again to solve the mystery.

First Date Tip #9:

Skip the kiss. It’ll let you feel more calm and confident throughout the date, spare you both some awkwardness at the end, and maybe even make her more excited for date number two.

Closing Thoughts

One of the reasons first dates used to feel so intimidating to me is because I didn’t have much dating experience—and I definitely didn’t know any of the stuff I shared above.

By learning from my experience, you can avoid my ignorance (well, some of it anyway), and skip to the part where dating becomes a lot more fun than it is fearful.

Good luck! And let me know how it goes: dave@irreverentgent.com 

14 Foolproof First Date Questions
(Plus! 37 Follow-up Questions to Keep the Conversation Going)

Enter your email address below to get 14 fun conversation-starting first date questions sent straight to your inbox.

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