First Date With Younger Lady - What to Wear?

DressPRMex · Feb 23, 2006

quote:I'm 35 she's 22. I'm not thrilled with the age difference ... We're just going to see a scary movie and grab some ... I asked her if she had any problems with the age difference and she said no.

Mark:

First of all, donâ€™t try to impress us with the â€œIâ€™m not so thrilledâ€ drillâ€¦ C'mon, you MUST BE THRILLED, if not for the age difference itself, at least for having a shot with a 22-year-old!!! You are one lucky man, for all I care. 22???? Mmmmmhhh [

], as my Aunt puts it when she talks about 22-year-olds: "pure abalone"

Plus, SHE doesnâ€™t seem to have a problem with you being 13 years her senior. There are a couple of 22s in my office whom I can only sigh aboutâ€¦ After all, I do have a ring on my finger and I do love my Wife to death.

In any case, I do like your clothing option, but Iâ€™d also like to suggest the sport coat sans a tie, with 501s. Also, I think girls do prefer the super luxurious shirt sticking out of the jacket instead of the sweater that screams â€œMamaâ€™s boyâ€.

PLEASE: Donâ€™t do t-shirt and jacket. That is trying too hard (and you don't want to look like Don Johnson in Miami Vice)

Good luck and do let us know how it went!!!

Mike Petrik · Feb 23, 2006

Black shirt, black blazer and especially black pants. Add some serious bling (not too much -- don't want to look too trendy) and a pair of black square toe shoes, and you're set.
P.S. Weather permitting make sure the shirt is short sleeve so that when you remove the blazer she can see you tat.

DukeGrad · Feb 23, 2006

VM

LOL
Had to get my two cents in on this one!

Have nice day

Jimmy

burnedandfrozen · Feb 23, 2006

Well, here's a bit more info. She's a single mom who moved back to her parents. She had her daughter when she was 17. During the times we've talked, she said it was a foolish thing getting pregnant at that age to a guy she thought she loved (didn't we all think we were in love at 17? I sure did!) who then split. She works two part time jobs. She adores her daughter and introduced me to her one day. My friends say she's looking for a Daddy substitute but somehow I'm not getting that vibe from her. I'm just going to play it casual and see how things go.
So far I'm nixing the spectators. It's been kind of cool in LA these days, so I'm probably going to go with a sweater, flat front pants and my Guci horse bit loafers. I do actually have square toe lace ups but I have no idea where they may be. The untucked striped shirts idea is good, but I only wear untucked shirts with shorts and it's too cold out for that. I'm also thinking of a really cool Issey Myaki (sp) sport coat that has a odd but interesting lapel and a dark green nubbly finish. I may wear this with a white T and grey flannel pants and the loafers. Basically what I would normally wear I guess. Thanks again for all the great advice.

Bradford · Feb 23, 2006

I'd say skip the spectators - too old mannish. But other than that, stick to whatever your normal style is. If she's agreed to go out with you, just be yourself because that's what she likes. If you are the type of person who normally wears jeans outside of work, then wear jeans on your date. If you would never be seen in anything other than flat-front pants, than wear those. Don't try and ape the style of someone else - just be yourself.

DressPRMex · Feb 23, 2006

Issey Miyake

I used to work for the guy.

Mike Petrik · Feb 23, 2006

Seriously, I think Bradford gives good advice. My hunch is that you would have to wear something really weird (and you are clearly too sophisticated to do that) to hurt yourself. She is probably much more concerned about what she wears, and be sure to compliment it.

Misia · Feb 23, 2006

I just joined this forum and I had to reply. I think I might be the only woman on this post...

When I was 21-22 I dated a lot of older men as well as younger ones. If she accepted a date with you, then she might be looking for something a little different than what she's used to, so I would ignore trying to find out what she's "used to" and simply try to figure out what she would enjoy. And please don't take her to a chain drinks place. If she's a girl like me, she might think that you don't think much of her. If she likes and respects you, she wants to recieve messages that you think a lot of her too.

As far as what you should wear, if you dress down too much or too young it can send several wrong messages. First off, you might come off as foolish for attempting a style that doesn't suit you. Secondly, and worse, she might interpret a sudden dressing down for her as silent commentary on what you think of her.

Trogdor's advice sounded like a good variation of your second suggestion, and your first suggestion sounded good too, but I would go without the spectator shoes. I wouldn't suggest wearing a t-shirt at all.

This stuff should be common sense and I'm sure that you wouldn't make these mistakes, but some of the men I dated did these things: The biggest way that you could make her feel like your her father is in what you say and the attitude that you convey towards her. Be mature, but don't act "Maturer than thou". It's just as annoying as any other self-righteous attitude. In conversation, try to avoid making generalizations about young men and women, such as the generalizations I've read here in these posts. Believe it or not, not all young men and young women are the stereotype. Act like you believe that last sentence. She wants to be thought of as a unique person with a unique set of experiences whom you respect. When older people respond with "everyone feels like that at your age" it sends openness to a screeching halt. When she vents or complains about something, don't give fatherly advice. Just listen. Then maybe tell about some time when something similar happened to you. Or make a joke. Only advise if she specifically asks, "What do you think I should do?" Totally avoid the phrases "when I was your age" and "at your age". Don't make her feel like her decisions, opinions, and attitudes are substantially dependent upon her age, and she might not be inclined to look at you the same way.

burnedandfrozen · Feb 23, 2006

Actaully, DressPRMex I'm really don't like the idea of dating someone this young. We are of different generations....what on Earth will we have in common? I'm getting to the age where I'd like to find someone to settle down with and start a family. I can almost bet it's not going to be a 22 year old no matter how hot she is. I'd rather date a woman in her 30's but most are married and the few that aren't had drug problems, ex-husband problems ect.
So lets see ok no T under a sport coat either. This is actually getting difficult since there's not much left. Maybe a black V neck with jeans? Sounds about right.

burnedandfrozen · Feb 23, 2006

Welcome to Ask Andy Misia! It's always nice to get a ladies perspective. Stick around, we have some great people here and we have lots of fun on this board.
DressPRMex you used to work for Miyake? Please tell us more.

kabert · Feb 23, 2006

quote:Originally posted by burnedandfrozen

Actaully, DressPRMex I'm really don't like the idea of dating someone this young. We are of different generations....what on Earth will we have in common? I'm getting to the age where I'd like to find someone to settle down with and start a family. I can almost bet it's not going to be a 22 year old no matter how hot she is. I'd rather date a woman in her 30's but most are married and the few that aren't had drug problems, ex-husband problems ect.
So lets see ok no T under a sport coat either. This is actually getting difficult since there's not much left. Maybe a black V neck with jeans? Sounds about right.

Move to DC -- there are loads of women in their early to mid-30s here who are attractive, have plenty of money (and good jobs), are well educated AND are unattached (but would like to settle down).

Long Way of Drums · Feb 23, 2006

I suggest a navy blazer and a bright, neon orange camo ringer. When this is evidently confusing and embarrassing, turn it inside out, put it back on, grab your jacket, and ask her to cut off the tag. I'm sure it'll work out.

"Und wenn du lange in einen Abgrund blickst, blickt der Abgrund auch in dich hinein."

"Love. You can learn all the math in the 'verse, but you take a boat in the air you don't love, she'll shake you off just as sure as the turning of worlds. Love keeps her in the air when she oughtta fall down, tells you she's hurting 'fore she keels. Makes her home."

We will not walk in fear, one of another.

MrRogers · Feb 23, 2006

quote:Originally posted by burnedandfrozen

Actaully, DressPRMex I'm really don't like the idea of dating someone this young. We are of different generations....what on Earth will we have in common? I'm getting to the age where I'd like to find someone to settle down with and start a family. I can almost bet it's not going to be a 22 year old no matter how hot she is. I'd rather date a woman in her 30's but most are married and the few that aren't had drug problems, ex-husband problems ect.

So why are you going out with her?

MrR

"Give me the luxuries in life and I'll gladly go without the necessities"

Doctor Damage · Feb 23, 2006

quote:Originally posted by kabert
...the 6 or 7th date, after you've got her hooked...

That's all it takes?

I once went out with a woman who was 29, when I was 32. She asked me "So, what's it like being 32?". The snotty reply would have been, "Yer gonna find out soon enough, babs!" I payed no attention to the question, which was a mistake because it would have been a warning to walk away (accurate, in the end).

I think the trad thing might be OK, assuming the girl has a reasonably broad mind. She might think you're being retro-ironic (little does she know!). I've often wondered if the trad style twinned with an old flat-top haircut might allow one to pull retro 50s girls, rockabilly types...maybe some of our British trads could comment.

DocD

thinman · Feb 23, 2006

quote:Originally posted by Misia

I just joined this forum and I had to reply. I think I might be the only woman on this post...

When I was 21-22 I dated a lot of older men as well as younger ones. If she accepted a date with you, then she might be looking for something a little different than what she's used to, so I would ignore trying to find out what she's "used to" and simply try to figure out what she would enjoy. And please don't take her to a chain drinks place. If she's a girl like me, she might think that you don't think much of her. If she likes and respects you, she wants to recieve messages that you think a lot of her too.

As far as what you should wear, if you dress down too much or too young it can send several wrong messages. First off, you might come off as foolish for attempting a style that doesn't suit you. Secondly, and worse, she might interpret a sudden dressing down for her as silent commentary on what you think of her.

Trogdor's advice sounded like a good variation of your second suggestion, and your first suggestion sounded good too, but I would go without the spectator shoes. I wouldn't suggest wearing a t-shirt at all.

This stuff should be common sense and I'm sure that you wouldn't make these mistakes, but some of the men I dated did these things: The biggest way that you could make her feel like your her father is in what you say and the attitude that you convey towards her. Be mature, but don't act "Maturer than thou". It's just as annoying as any other self-righteous attitude. In conversation, try to avoid making generalizations about young men and women, such as the generalizations I've read here in these posts. Believe it or not, not all young men and young women are the stereotype. Act like you believe that last sentence. She wants to be thought of as a unique person with a unique set of experiences whom you respect. When older people respond with "everyone feels like that at your age" it sends openness to a screeching halt. When she vents or complains about something, don't give fatherly advice. Just listen. Then maybe tell about some time when something similar happened to you. Or make a joke. Only advise if she specifically asks, "What do you think I should do?" Totally avoid the phrases "when I was your age" and "at your age". Don't make her feel like her decisions, opinions, and attitudes are substantially dependent upon her age, and she might not be inclined to look at you the same way.

Welcome to the forum Misia! I like all of your advice. I've met 20-year-olds who are more mature than many 50-year-olds I know. Some people can learn from their life experience as well as that of others; some people never learn and never grow. Judge people as individuals, not as members of a group.

Edit to stay on topic: Wear whatever you would normally wear on a first date (but please, no spectators). You'll be comfortable and project the real image of yourself. If she can't handle the real you, find out now, not after you've invested significant time and effort.

Best regards,
thinman

DressPRMex · Feb 23, 2006

quote:Originally posted by burnedandfrozen

Actaully, DressPRMex I'm really don't like the idea of dating someone this young. We are of different generations....

Mark:

You have to appreciate that my tone was in good humor. Of course I understand that one should aim at being with someone of similar age in the long run for all the reasons you describe. Such is my case, since I am only three years older than the Wife.

Regardless, if you have no commitments right now, I think you should take advantage of the opportunity. Who knows? You may find someone incredibly clever and well-seasoned for her young age, and then again, you may later also find another older woman who is as naÃ¯ve as a 5-year-old (Remember Dylan's "Just like a Woman"?).

Enjoy your evening out and, as for the black v-neck with jeans, a lot of people here will be against jeans plus black shoes, including myself, so you may want to swap the black v-neck for another color (navy, maybe).

Goblin · Feb 23, 2006

quote:I think the trad thing might be OK, assuming the girl has a reasonably broad mind. She might think you're being retro-ironic (little does she know!). I've often wondered if the trad style twinned with an old flat-top haircut might allow one to pull retro 50s girls, rockabilly types...maybe some of our British trads could comment.

In my experience with the kind of girls who are into the rockabilly look, the entire "trad" affectation is too, well, Poindexter-ish. They go for more of the skinny hipster-"rebel" types.

The trad thing would probably go over famously with emo girls.

This may vary by local scene.

Holdfast · Feb 23, 2006

I had a few dates with a lovely 22 year old girl about a month or so ago (but I'm only in my late 20s so the age difference wasn't that big), and she joked that one of my sports coats made me look like her professor.

Hmm...[xx(]

I also found it very difficult to not give advice, though I dd manage to avoid falling into this trap! Took a fair bit of willpower though.

Having said that, my clothing wasn't the reason things didn't work out, so I wouldn't alter your clothing too much...

. Spectators though? No way!

Finally, good luck, you lucky boy![8D]

shuman · Feb 23, 2006

Might I add, since you work in the same company, even apart, rest assured she has asked others about you. Be yourself. That is what she is interested in. Also, most single moms are concerned that their child will turn away any would be suitors, so respect her and her child. Maturity is good. Good luck. Let us know how it goes!

NewYorkBuck · Feb 23, 2006

Im 37, my gf is 25. We met when we were 34 and 22. Since meeting her, she has convinced me to wear seersucker, madras, and shetland sweaters - all classics. Moral of the story - depends on the lady more than her age.....

First Date With Younger Lady - What to Wear?

DressPRMex

Mike Petrik

DukeGrad

burnedandfrozen

Bradford

DressPRMex

Mike Petrik

Misia

burnedandfrozen

burnedandfrozen

kabert

Long Way of Drums

MrRogers

Doctor Damage

thinman

DressPRMex

Goblin

Holdfast

shuman

NewYorkBuck

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