Relationship advice

Here 20 Things Each Man Is Worried About On His First Date With Her

While he may have a cool and calm exterior, that by no means is a true reflection of how he feels on the inside. He may look like he is totally relaxed and at ease on his first date with her, but that doesn’t mean he isn’t stressing and over thinking all his fears and worst nightmares projected onto his first date.

He wants this date to run just as smoothly as you do, but what you may not have guessed is that he feels more pressure to please than you may. As a guy, he feels it’s his role to conduct the date and make sure everyone’s having a good time. On top of supplying the ideas, conversations, and fun, he also has to worry about the way he looks and what you are thinking of him from moment to moment. Don’t underestimate how much he cares, he’s more on edge than you may expect. We went around and asked several guys what their fears and anxieties are before and during their first date, and here’s what we found out.

Does He Smell Okay?

Did you know that when you’re nervous, chances are your breath might be less than minty fresh? According to Wikipedia, when you’re stressed your mouth actually dries out the saliva causing less than cute bacteria to build up in your mouth and wrecking havoc on all those breath mints you’ve ingested. So if he’s stressed about your date, most likely he’s also stressed about his breath. Not to mention his high expectations for the end of the night where he has every intention of keeping his opportunities wide open. He might be more concerned about his breath than he’s giving off.

How His Hair Looks

While it may not seem like a masculine fear, men are just as concerned with how their hair looks as women are. Okay, maybe not all men are, but maybe not all women are either. We just don’t want you overlooking how much time and effort he may have put into his hair. And, when he goes to the bathroom ‘real quick’ he may be checking out his do and rearranging his look with the same amount of time and consideration as you would. It’s time to bring back the 1950’s Grease comb, and comb back that hair without shame or stress.


Making Sure He’s Being A Gentleman

The rules for how a man should treat a woman these days are growing blurrier and blurrier. While way back when it was very clear how a man and woman should behave (uptight?) now men no longer know what to do without overstepping (or under-stepping) what’s expected of him. He may be over-thinking it, ‘Should I hold open the door for her?’ He may have too many doubts and questions circulating through his head that he may even forget to do the basic acts expected from person to person. So, beware, his inactivity may just be fear based.

How Cool Is Too Cool?

As the old game goes, it seems everyone likes it when the other plays hard to get. Many girls were whispered by their mothers and grandmothers to play hard to get when it comes to the man they desire, but little did they know men would learn to play the same game. On his first date with you, he may be stressing how to play it cool, without acting too eager, or too nice. After all, he doesn’t want to be labeled as ‘the nice guy’ that could easily be every guy’s worst nightmare.

Laying It On Too Thick In The Romance Department

He may be thinking about different styles of romance and charm to win you over on the first date. While flowers are the go-to for many guys, he may be worried that it’s too much or even cliché. He wants to do something that will make you feel special and adored, but he doesn’t want to overdo it and scare you off. Many guys have the urge to be romantic, or want to learn to be romantic but are too afraid it will turn off the very girl they are trying to win over and guess what, that girl is you.


Not Looking Like His Profile Picture

More and more of us are meeting each other on dating applications and websites (or are dating websites obsolete at this point?). With that said, he knows that the only way you have of recognizing him is based on his profile photo. Men have a hard time telling what they look like in their photos and if they are actually true to what they look like on the every-day. If you’re meeting for the first time in real life, he is probably really anxious and worried that you may find him less attractive than his profile picture.

Will He Be Tall Enough If You’re In Heels?

Again, if you are meeting for the first time in real life, and you’ve only been communicating over your phones, and haven’t made any physical contact yet, he may be self-conscious about his height. Of course, if he falls into the 6’2 category, he might not be too concerned, unless of course, you’re 5’1 and aren’t a fan of a huge height difference. In the case where he’s not confidently tall, he may be self-conscious that he is shorter than you had expected. Typically, not a fear for a woman, but a big fear for many men.

Making The Right Call For A Casual Or Fancy Date

You’re probably not best friends going out on a date for the first time, and if you are, this can still be a fear of his. But, if this is the first time you’re meeting, he knows the date plans are up to him. Now, he’s stressing if he should impress you with a romantic and luxurious night out, or if he should keep it chill and casual to keep the pressure at bay. If he knows what kind of girl you are, he will know how to charm you best, but if this is your first time meeting, he might not know which direction to go.

Will She Be Bored?

Making the conversation flow on a first date is no easy feat. If he’s naturally confident and funny, this probably won’t concern him, but the chances are he’s not all that self-assured in this very situation. He may be worried if the conversation is boring you, afraid you’re not interested in the topics he’s bringing up, or the way he’s explaining his ‘super thrilling’ story. Then he can leap into the fear of overdoing it and talking too much, what’s that expression? Chewing your ear off? Right, he definitely doesn’t want to do that.


Is He Actually Funny?

Every girl loves a funny guy, right? He wants to make you laugh, he wants to see you smile, and if he doesn’t he may grow insecure that he isn’t as funny as he thought he was. The easiest way to charm a girl is by using your sense of humor, but if you don’t have one, you’re really out of luck. If he’s not absolutely confident about his ability to make you smile, he may be squirming in his seat afraid that you find him totally boring, and not fun at all. While you may have overlooked this trait, he certainly won’t.

Money, Money, Money

Does the modern day woman want to go halfsies on the bill? Will she be offended if I offer to pay the whole thing? Will she be offended if I don’t go straight for the bill and cover it before she gets a chance to take out her wallet and offer to split it? These are all the worries running through his head before you even thought of asking for the check. If he doesn’t know you well, in these contemporary days, he won’t know how to handle the bill. He’ll want to be smooth about it, but he won’t know which way is the right way with a girl like you.

What If She’s Not Into Me?

He may be worried that you’re not into him within the first 10 minutes of the meeting, he may be worried you’re not into him after the first hour of meeting, and he may be worried you’re not into him a day later when the first date is finally over. What might strike you as his disinterest in you, may actually be his insecurity of how into him you actually are. If he really likes you, (which we hope so!) he won’t know how to tell if you’re into him or if you’re just acting nice. How can he tell the difference between politeness and interest?!


What’s The Right Amount Of Space To Give Her?

Some guys are over-aware of their hands and how much contact they are making with their girl. They may be afraid to hold your hand or hug you hello. He doesn’t want to overdo it and make you feel uncomfortable, just in case you’re not into him, or you’re not much of a hugger. He may be stressing out (on the inside) where and when to place his hands on what and who and how, how, how? He doesn’t want to make you uncomfortable and doesn’t want you to get the wrong idea about what kind of guy he is. Tricky.

Are His Clothes Ok?

He may look like he just threw something on, a tee shirt that was just lying around on his bedroom floor, but in actuality, he cares, he really cares. He might be stressing that you don’t like his tee shirt, his belt, or that his jeans are too big or too tight, who knows these days? There seems to be no limit in how tight men’s jeans can get, but maybe you are into loose legged jeans, or maybe he should have dressed up and worn a button-down shirt? He may try to approach you casually, but he is definitely over-thinking his style and his first impression.


Is There Something In His Teeth?

Everyone’s worried about having food on their face or in their teeth on the first date. Even though he may avoid anything too messy and not order finger foods, he may still worry by the end of the meal if he has some embarrassing leftovers by his nose, cheeks or lips. He doesn’t want to be left out of the secret, but he probably doesn’t know how to ask you on your very first date if he has something he should know about. The two of you are probably stressing about the exact same thing in the exact same moment, what a relief.

How Does She Feel About Facial Hair?

Many guys are proud of their facial hair, but sometimes they just get too lazy to clean up their awkward patches or trim it when it gets a little unruly. There are also those guys who forget to shave under their chin and close to their neck. He may be worried that he slacked in the shaving department. Maybe you prefer a guy without a mustache and beard, or maybe he should have grown a mustache or beard because it seems to be a trend that just won’t go away. What is she into? Can you believe he’s actually over thinking it? If only he knew how long it takes to shave our legs.

Inviting Her Over

So, the night is coming to an end, it was overall a nice night, you had a good time, he had a good time, now what? He wants to see you again, he wants to see more of you, but he doesn’t know if he should invite you over for a nightcap, or a cup of tea, right? Maybe he wants to keep talking to you, he’s enjoying his time with you, but he doesn’t know what you’re actually expecting by the end of the date and if you’re expecting anything at all. How can he take things further without overdoing it?

How To Know When The Night Is Over

During the night you may be enjoying a simple activity, like walking along Venice beach or walking through the city. When the meal is over and the activity has come to an end, he may not know the exact moment to split ways without making it look like he wants to leave. How does he leave while leaving you wanting more? There is only so much that can be accomplished in the first date, and maybe everything was going right, up until he made the final mistake of leaving in the wrong moment. How can he tell when she’s ready to go and where she wants to go exactly?


What’s The Appropriate Goodbye?

Of course, you knew he was thinking about the kiss all night long, probably before he even met up with you, and now that moment has come. How does he do it smoothly? Should he do it, or should he be a gentleman and wait? How does he know if you’re into him, interested in a simple kiss, or if you’d rather wait until the next date? No one likes the feeling of getting rejected, the blow is too rough for the ego to handle. Now he has to consider what to do and how to do it.


How To Approach The Second Date Conversation

Could he already be considering the next date opportunity? He may be stressing when to text you next, when is too soon and when is too late? He could be thinking about you all night and all through the next day but he doesn’t want to come off as too desperate, he wants to play it cool, but he also wants to know if you felt the same way. Again, he doesn’t want to get rejected, he wants to wait and see if she will maybe even contact him and make this whole thing easier, or maybe he’ll be brave this time and let you know, ‘Hey, I had a really good time the other night, would love to see you again.’ It’s so simple, yet they sometimes forget how easy it is.


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