Dear Wendy
Dear Wendy

How do I properly communicate with women?

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Viewing 12 posts - 661 through 672 (of 1,144 total)
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  • #859211 Reply

    Yeah, I would second this. Social skills and comfort and confidence are muscles that need to be exercised. Dating can’t be your only social outlet.

    #859239 Reply

    Kate: For clarification, are you saying that the blazer and the pants should be different colors? Or can they be the same color?

    Also, are you suggesting this is a look for dress pants (not chinos)?

    #859243 Reply

    Yes to the dress shirt, blazer, and pants comment from Kate. I work in a busy part of the city and see a TON of men dressed this way. The standard business appropriate casual friday attire is a blazer or collared zip up, dress shirt, and dark jeans. This would be perfectly acceptable date and photo attire while achieving the same level of polish/formality as the dress shirt/tie/no suit jacket combo (yuck). A nice modern coat is also a must this time of year since someone’s first impression of you will likely be outside of a restaurant or coffee shop.

    Robert, I can try to meet you another day. Availability runs thin this time of year, and I’m glad you have photos scheduled- that’s a very important step. If you want a few casual cell phone shots in addition let me know and we can try to find some time.

    I agree that counseling is something you should make time for. Nearly everyone I know has gone at some point, including me. It is so helpful. And check out or groups related to activities you like. There are sooo many options in Pittsburgh. We have many friends who play dodgeball in a rec league weekly, my husband chaired the Three Rivers Paddling Club for several years (they sponsor formal and informal meetups for white water kayakers and put on several clinics for beginners every year-and had new members join all the time), I actually used to be part of a young professionals meetup who did happy hour monthly, and CCAC (community college for the county where Pittsburgh is located) offers so many classes that are either one time or a short series from everything from taekwondo to cooking- I’ve taken bread baking and cake decorating courses, and did a psychic abilities one once for kicks. So I know there are tons of opportunities in Pittsburgh. Hell you could probably start one for all the Christmas shows. The point is, maybe it’s time to make your life a little more full in general. And the more out there you are the more likely you are to meet people who will become great friends.

    #859244 Reply

    Stop focusing on the clothes, Robert. Don’t wear the suit. Or wear all your new stylish outfits and take one picture at the end in the suit. Or yeah, just the suit jacket.

    Make an appointment for a therapist. Join meetup. Make your own meetup group for holiday events. Volunteer at a holiday event.

    #859248 Reply

    Meetup and volunteering are both nice ways to meet people. You have an activity to do yet can talk while doing it. The activity itself can be what you talk about first so gives you something in common to discuss. You also might be able to join a group for small business owners.

    Are there any holiday events in your community that need volunteers? Lots of things depend on volunteers.

    #859252 Reply

    Robert, you can literally use Google, Pinterest, and YouTube to find outfit help! You can find styles that feel true to you but are more modern this way.

    And I will say, I think it’s very odd that all your friends flat-out ditched you. The worst I experienced was the situation described here, but we are still friends and she’s pretty much the only friend I have who retreated into her relationship that intensely as an adult. But, like I said, I do think her situation was unique because she was a late bloomer. If all your friends flat out do not want to be friends with you after meeting an SO, the friendship was never a deep one meant to last to begin with IMO.

    #859301 Reply

    Today’s JCrew Golden Deal, right up Robert’s alley of what he should wear.

    Ignore the business look with the tie Robert. The rest, good options for current dressy. So, key take-a-ways should be:

    Slacks or jeans with
    1. A sweater or button up + blazer or sport coat, or
    2. Button up with a sweater
    NO TIE

    Also take note of the clean lines, slim fit. That’s what you want.

    #859336 Reply
    avatarMiss MJ

    Kate: For clarification, are you saying that the blazer and the pants should be different colors? Or can they be the same color?

    Also, are you suggesting this is a look for dress pants (not chinos)?

    Not @Kate: but, the blazer and the slacks need to be different colors and the blazer needs to be darker than the slacks. Blue blazer, brown or tan slacks. Black blazer, gray pants. (Or dark blue jeans with any of these!) Lighter shirt – subtle coordinating patterns preferred – matching belt and shoes (brown with the blue/tan combo; black with the black/gray one – belt and shoes must match)and NO TIE. NONE.

    The only time you should ever wear a tie is with a suit and if you’re in court or at a wedding. Otherwise, forget it.

    #859384 Reply

    Oh man, we’ve been over and over this. It’s a great look for dark blue jeans or chinos. The jacket should not look like it’s trying to be the same color as the pants.

    Miss MJ had good suggestions above. The “finance guy” look, at least in Boston, is a dark blue blazer with a pattern in it, a dark blue jean, and a light blue shirt. Or it might be blue chinos, but because the blazer has some kind of a check pattern and a different texture, it doesn’t look like a wanna-be suit.

    I wear black pants, say, to work. If i want to put together a dressy outfit, I don’t wear a black blazer, because that just becomes a mismatched suit. But I can wear a jacket with a pattern or texture that has black in it. Or I can wear a camel jacket. Or some type of nice cardigan. Or a dress and jacket / dress and cardigan. Coordinating or complementary, not matching. I wear a suit for interviews only.

    Please please stop with the “dress pants.” These aren’t a thing anymore. There are suit pants, that you wear with a suit. And there are jeans and pants for everything else.

    #859388 Reply

    I had the chance to go into Target earlier this evening. Didn’t buy anything, but looked around to get some ideas for three outfits for the photoshoot (in a few cases, I just needed the skus for what I already have because I couldn’t find them again on the website).

    I found KTFran’s and MissMJ’s posts after I got back, and those helped with the selection of the dressy outfit. Here it goes…

    Dressy outfit:


    I have this in blue already, my second choice WAS bayshore blue, but after Miss MJ’s post, I am wondering if I should use grey

    Jacket, in black

    Pants, in grey. Though, could I use the grey suit pants I already have? I am not sure I can get these from target. There is a Macy’s in the same mall and a Kohl’s in the shopping center next door that have grey dress pants.

    Shoes, I already own

    and black belt, of course.


    Dressy-casual outfit:

    top (I already own). Mine is not coming up on the website, but same design, except white background and grey dots

    chinos. own black, but would like navy

    shoes (same as above)


    casual outfit

    top (I own this one)

    black jeans (I own these)

    shoes (I own these)

    Okay outfits?

    For headshots, I will switch out various tops. You all liked the tops I got.


    Golfer.Gal: Thanks. I’ll keep you posted. There are extra things during the Holiday season people (including me) are involved in, so I understand that.

    BTW, if you’re interested, KDKA radio (AM) at various times throughout the day is giving away VIP indoor passes for the Santa Spectacular, and they say you would have a clear view of the 7:45 fireworks. I’ve heard Lynne Hayes-Freeland and Robert Mangino give them away on their shows, not sure if Marty Griffin or Wendy Bell do so as well. You’d just have to be the correct caller when they announce it.

    I saw a story about that paddling club, on channel 4 I think, at least 4 or 5 years ago.


    Robert, you can literally use Google, Pinterest, and YouTube to find outfit help! You can find styles that feel true to you but are more modern this way.

    I have done this, but contradictory things come up. You and the others here are mostly consistent, so I’ll tend to trust the consensus here.

    For example, this look came up when I searched Pierce Brosnan fashion, as several here have suggested emulating, but everyone was against both the polo shirt and the tan khakis

    Multiples of these came up when I searched “men dressy attire”, a look liked even less

    That’s why I tend to trust the consensus here.

    And I will say, I think it’s very odd that all your friends flat-out ditched you.

    Agreed. They all did what your one friend did to you. Your loyalty in that situation is amazing, I have to recognize that. Me, in that situation, would understand that a lot of her attention will be there for quite a while, I would just want to talk to her every so often to see that she is happy, and to be invited on a few double dates would be nice, too, but none of that has ever happened for me. I’ve been hurt worse in friendships, honestly, than in any of my dating experiences.

    #859391 Reply

    With the zip sweater, you should have some kind of shirt on underneath. It can be a button-down shirt or a colored tee shirt.

    The black jacket is a little tricky because it’s a suit jacket, not a sport jacket / blazer meant to be a separate. It would look good with *dark blue jeans* or maybe grey chinos. Or if you had a grey pant with some kind of subtle texture or pattern. I would not pair it with your suit pants, I just don’t think that’s a good look. Again, it ends up looking like you were trying for a suit and not making it.

    #859392 Reply

    If you go to and search “men’s blazer,” you get all these looks that would be soooo perfect for you. I love the guy in the camel jacket. I’d go on a date with him. Yeah I know it’s the same guy in all the pics but I like that outfit. You have the same coloring as me, and I look great in camel.

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