Pocket Square on 1st date = Trying too hard?

[Bartolo]

Originally Posted by Doxe

I can guarantee you that on a first date she's not wearing her ratty cotton underwear that has been washed a thousand times. She's wearing something that makes her feel sexy and strong.

You may have not been on many first dates lately. It's a jungle out there, and I mean that in a double-entendre kinda way.

Even women who truly appreciate men in nice clothes will be swooning over the mere fact the OP isn't wearing New Balance shoes, Dockers and/or Ed Hardy. The ps can be used to 'step it up' if she gets a second date.

 

[Drudged]

Originally Posted by acecow

I wore a pocket square today. But I meant for a first date, if he wants to make a certain impression, maybe it's a little too much to wear a pocket square. Actually, I'm pretty darn sure it is. A typical girl will not be able to appreciate it and will probably think less of him. I'd save it for the second date, when the first impression has been made. No one claims you cannot be stylish with a slightly simpler choice of accessories. Where we live, a nicely fitted sport coat would already be standing out.

All I see is orphaned jackets with jeans nowadays. Hell, half the people at a concert today wore t-shirts. I think I was the only one in the whole damn place with a pocket square. Felt good.

I'm glad to hear that there are others around here that take pride in what they wear, because you sure wouldn't know it from a general observation! I'll bow out of the advice giving aspect of this thread due to my own biases. I love little quirks to outfits that make them stand out, though never in an overt way. On a first date, a pocket square might be overkill depending on what the girl is used to. However, I am quickly learning that there are plenty of beautiful women in the world to become acquainted with. If a wearing a pocket square is too "over the top," and she cannot become convinced otherwise, then any further effort into developing said relationship was not worth your while anyway.

Keep in mind that my perspective is that of a 22 year old originally from northern California male. I take pride in the way I look (and do aspire to dress like many of the senior members on this forum - monetary constraints be damned), however find that many of the women my age are intimidated and do not know how to react to a well dressed, well composed man who acts as a gentleman. Those rare few that do appreciate it, and who are not intimidated are often the most interesting of the lot. Keep in mind that the mere fact that you are debating whether or not to wear a pocket square to a first date puts you leagues beyond the average male. This is not something to be ashamed of, and I stress the fact that you should dress to make yourself comfortable in this circumstance, confronting any obstacles later should they arise.

 

[Doxe]

Originally Posted by knezz

Or she'll spend the rest of the evening punching you out for being fresh...

Good thing I'll have a pocket square to soak up the blood

Seriously though, a couple of months ago the girlfriend was talking to one of her single friends who was going out on a date with a guy she liked. They were discussing what sort of date it was, i.e., serious, casual etc. The friend said that it was a casual date but that she was "interested". I asked what that meant and she replied, "Well, it's not like I'm going to get waxed for him, but I'll wear something nice underneath just in case".

I've got a friend who works for Microsoft as a project manager. She told me she wears sexy lingerie under her conservative business suit when she has an important meeting because it makes her feel powerful and strong.

With my nephew it's Spiderman underoos. To each their own.

Chances are that if she's on a date she's not schlepping it in granny panties...and if she is, then "no dice".

 

[Hehlol]

I'll have to start posting here whenever I HAVE A DATE FRIDAY!

It's amazing to me that anyone who has to ask the Internet if they should wear a pocket square on a date...gets dates.

 

[Doxe]

Originally Posted by Hehlol

I'll have to start posting here whenever I HAVE A DATE FRIDAY!

It's amazing to me that anyone who has to ask the Internet if they should wear a pocket square on a date...gets dates.

 

[Don Carlos]

Originally Posted by Doxe

I've got a friend who works for Microsoft as a project manager. She told me she wears sexy lingerie under her conservative business suit when she has an important meeting because it makes her feel powerful and strong.

I'm calling BS on this for two reasons:

a) Nobody at MS (at least in the home office in WA) wears a suit to work;
b) This is precisely the sort of thing that cute chicks in nerdy professions say to guys all the time to keep them under their thumbs.

EDIT: I think I missed the "important meeting" part of your post, so maybe "a" doesn't apply.

 

[Doxe]

Originally Posted by Arrogant Bastard

I'm calling BS on this for two reasons:

a) Nobody at MS (at least in the home office in WA) wears a suit to work;
b) This is precisely the sort of thing that cute chicks in nerdy professions say to guys all the time to keep them under their thumbs.

EDIT: I think I missed the "important meeting" part of your post, so maybe "a" doesn't apply.

She's not in WA. There's very few women in her position so it may be her way of empowering herself. She mentioned that the number of men at MS wearing pleated chinos that are 3 sizes too big are legion.

My nephew wears Spiderman underoos because be believes it makes him stronger and run faster. But he's 7.

I stick to my original post.

 

[JayJay]

Originally Posted by DocHolliday

Just be yourself. If you normally wear pocket squares, then she might as well know now rather than later.
This.

 

[Tibor]

I can only speak for myself, but if I don't wear a pocket square on the first date, and I end up getting laid, I probably don't deserve it.

I went to a Funky Disco-House party at a wine bar last night. Some girl comes up to me and takes my pocket square out, than a second girl comes up behind me, pulls my arms behind me as if I should submit, and a third takes a spare seat from a table next to the dance floor. The First takes my pocket square and blindfolds me with it, the second shoves me into the chair, and then the three girls proceed to have their way with me, blindfolded on a spare seat. I still don't know what happened to that pocket square, maybe they took it as a trophy.

Unfortunately, that pocket square was very sentimental to me as it was made for and monogrammed with my great Uncle's initials, who 70 years ago was a Hungarian Partisan Fighter and a survivor of 4 years in Auschwitz. I only hope that pocket square survivors the tyranny of those horny women.

Anyways wear the pocket square.

 

[Doxe]

Originally Posted by Tibor

I can only speak for myself, but if I don't wear a pocket square on the first date, and I end up getting laid, I probably don't deserve it.

I went to a Funky Disco-House party at a wine bar last night. Some girl comes up to me and takes my pocket square out, than a second girl comes up behind me, pulls my arms behind me as if I should submit, and a third takes a spare seat from a table next to the dance floor. The First takes my pocket square and blindfolds me with it, the second shoves me into the chair, and then the three girls proceed to have their way with me, blindfolded on a spare seat. I still don't know what happened to that pocket square, maybe they took it as a trophy.

Unfortunately, that pocket square was very sentimental to me as it was made for and monogrammed with my great Uncle's initials, who 70 years ago was a Hungarian Partisan Fighter and a survivor of 4 years in Auschwitz. I only hope that pocket square survivors the tyranny of those horny women.

Anyways wear the pocket square.

This made my morning.

 

[Don Carlos]

Originally Posted by Doxe

She mentioned that the number of men at MS wearing pleated chinos that are 3 sizes too big are legion.

Haha, seems about right.

My nephew wears Spiderman underoos because be believes it makes him stronger and run faster.

LOL, touche.

 

[83glt]

If you have to ask this question, I'm sorry but you will never find a girl to truly love you.

 

[83glt]

^^^
Wow, sounds like that PS really meant a lot to you, the way you let 3 filthy whores defile it and all. Good for you!

 

[83glt]

I think it's getting to the point now that wearing a pocket square doesn't make you stand out. Not wearing one is less the norm these days. Not saying it's a reason not to wear one, but there are a lot of poseurs out there now. Is it worth the risk of being taken for one of them? You decide!

 

[Tibor]

Originally Posted by 83glt

^^^
Wow, sounds like that PS really meant a lot to you, the way you let 3 filthy whores defile it and all. Good for you!

You do have a point..... In the sequence of last night's events:

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