Things Guys are Really Thinking on a First Date

There’s nothing like sharing thoughts with new people, so when Louie from the excellent Dating Woes and Ego Blows blog got in touch and asked me to write something for her I jumped at the chance. As with almost all dating blogs I’ve seen, DWEB is aimed at women, so I thought I’d mix things up a little and offer some of my own insight into what goes through a guys head before, during and after a first date.
So, on this Throwback Thursday, here’s the post that originally ran over there on 10 November 2017. Enjoy. Or not. I can’t force you either way. 😉

Like the ability to change a tyre, cook a tasty meal or secretly enjoying watching shows about dancing, over-thinking before a first date is not something confined to a single gender. In my experience, the only difference is that women are more likely to admit to their friends that they are nervous before meeting someone for the first time, or that they tried on a thousand outfits before settling on one of the first options considered.
Everyone gets butterflies going into a first date, including guys. The trick is trying to get them to fly in formation.
So, with that in mind, I thought I’d lift the lid on some of the things which go through the minds of the male half of a date. Obviously this doesn’t count for everyone, but some may be surprised that we’re not all as blasé, relaxed and cool as we try to appear


Holy shit! You’ve actually matched with someone! Wait, double check and make sure she wasn’t an accidental drunken swipe which in the cold light of day you’ll regret at first glance…no, weirdly she’s hot and still chose to match with you! She probably won’t message back, though. Let’s take a quick look at her bio and phtotos and craft a witty and interesting opening line.

No, delete that, try again. And that. You’re trying to be funny, not creepy. Right, press send. Then walk away – forget about it. Definitely don’t keep checking your phone to see if she replies.


She replied! Woohoo! No, play it cool. Don’t reply instantly. Give it a minute. Don’t seem too keen, otherwise she’ll think that you are desperate, and according to all those dating advice sites you secretly read apparently desperation isn’t sexy. What’s the right number of messages before you suggest meeting up? Over how long should they be sent? What if we send thirty messages over the next hour? Is that the same as sending ten over the next four days?! Why isn’t there a simple formula for all this?!

Arranging a date

Great – we’re on to arranging a date. She wants me to suggest somewhere. Needs to be somewhere cool, imaginative and interesting but not too weird and not too cliche. It needs to give her the chance to duck out rather than be trapped (so boat rides along the river are out) and give us an activity to do. Has to be evening too – no good dating story ever started with “we finished up lunch and headed back to the office…”.

I know – how about that cocktail bar with the indoor crazy golf bit? We can have a drink and can decide whether to play or whether to just drink more! You’re a genius!
She said yes! Oh, damn. Better start saving now – I totally forgot that drinks are super expensive there, and that’s without thinking about food or actually playing golf. Why didn’t you think about this before?!

Two days before

Okay, so we’re messaging a lot, that’s good, but is it too much? You missed her last message and then got caught up at work so didn’t reply for hours, she must think you’re playing games with her. She’s not replied to you all evening; she must be on another date. He is probably funnier, better looking and more successful than you are. He probably goes to the gym to further define his chiselled physique, and then drives his sports car to the orphanage to volunteer teaching kids how to read in between performing life-saving surgery at the hospital he runs. She’s probably having a great time with him. You were so close, only for her to find Zac Efron crossed with Toy Stark just before you meet and she falls for your Jimmy Fallon crossed with Hugh Grant schtick. What gave you any confidence you’d ever have had a chance, anyway?! Just look at yourself! You’ve not even shaved today! Your jokes aren’t funny and have the dress sense of Winona Ryder in the 80s.

No, wait – she’s messaged. She was out with her sister. Phew! And she’s still up for the date! Don’t come across as insecure. Play it cool. Confirm the time and place though. Don’t want to go to the wrong place. Again.

On the day

How hard can getting dressed be?!?! You do it every single day –  EVERY SINGLE DAMNED DAY, MAN!!! Just choose a shirt and put it on. No, not that one. It’s not ironed. Not that one, either. It makes you look pallid. There; a plain shirt. Nice. Do you roll up the sleeves or not, though? If you do she’ll see your lack of Dwayne Johnson-sized guns, but might notice your tattoo. Shit. You haven’t checked whether or not she likes tattoos. Schoolboy error. Okay, roll it up but keep it long enough to cover. Hair done, manscaping done (you should really do that more often, the bath looks like you attacked a bear with a beard trimmer), aftershave applied (probably too much, but some of it’ll wear off, right?!), shoes polished, teeth cleaned; you’re good to go.

Actually, go change your shirt.

On the date

Don’t say something stupid. Listen to what she’s saying. I’m serious, don’t say something stupid. But be interesting. Tell those funny stories from when you were travelling, or when you did that cool thing at work, but don’t brag. It’s not a competition. Damn, she’s gorgeous. Just look at her smile! Even when she’s talking, her eyes are smiling! They’ve got a way of sparkling, it’s as if they were lit up from within… Shit, you got lost looking at her smile and lost what she was saying. Stall! make time to work out how to change the subject!

Don’t look at her boobs, either. I mean, they are magnificent, but she’ll notice and put you in the same box as every other guy who only wants her for her body. You need to come across as noticing her good looks and appreciating them, but not over her personality. No, I’ve no idea how to do that. Improvise.
Seriously, don’t say anything stupid. You really want to see her again.

At the end of the date

Right, it’s gone well. You’re waiting for her Uber. Is this the time to try to kiss her? She kind of made eye contact for a fraction of a second longer than you thought she would normally, that’s a sign, isn’t it? And she’s swiveling on the spot a little. Or is that just her looking for her cab? What if you got it wrong and she’s not interested? Will she think you’re a creep? What if you’re actually a bad kisser after all? Wait a minute, you’ve totally forgotten how to kiss!!!

No, stop panicking, get a grip of yourself. Just put your hand on the small of her back, put a little pressure on, pull her close and go for it. Any second now. Go for it. It’ll work. No, it won’t. Yes it will. Probably. Quick, the Uber is only a two minutes away! Stop thinking about it and do it!

Later that night

See. It wasn’t that difficult! Now you’re walking on air like a teenager! It went so well! Wait, what if it was a sympathy kiss? What if she just kissed back so she could get away?! She noticed you looking at her boobs, didn’t she?! Idiot. You should’ve stayed locked on her eyes – that was the plan! And she probably hated your shirt too. Wait, you’re getting a WhatsApp message…

She had a great time and wants to meet up again! You legend! You didn’t mess it up! Well, you’ve not messed it up yet, anyway… Now, where to go to next? And what shirt to wear? And what to tell her about how much fun you had without seeming desperate?! Why aren’t these things easier?!?!

2 thoughts on “Things Guys are Really Thinking on a First Date

Add yours

  1. Brilliant! Always love your real life accounts of a guys mind. Definitely need more of this in my life! Women are only one half of a story, always nice to know the other too. Thank you.

    Liked by 1 person

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