Dear Wendy
Dear Wendy

How do I properly communicate with women?

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  • #855142 Reply

    I did stop in one shoe store near where I live that carries a number of things in wide width, and found two pairs. I didn’t get them yet, but they’re in stock, and was wondering if I could ask your opinions.

    For dress:

    For more casual:

    What do you all think?

    LisforLeslie: I am curious about one of your comments, you said that I am looking for a woman who is set in her ways, and you said it quite unequivocally. Why a woman who is set in her ways. I’m not saying you’re wrong, I just never thought that that was what I was looking for, and you seem to know.

    I did look back at my re-write, and see how it can come across as wishy washy, but there are many times I have no preference. For instance, there are times when I will want to do something specific, but other than that I don’t care what we do, as long as we are doing it together, whether it is something specific she wants to do, or we make something up as we go along, or we just stay in for the night. Based upon your comments I need to use a better word choice. Wendy is helping me with that.

    There is one thing I could be a little more unequivocal on, though, and that is that I do like to dress up. Prefer it, actually, but I did put in the part about being casual for the purpose of coming across easygoing, since i know I am in a minority on how much I really want to dress up for dates. Other than that, I can often go either way, but I do see where my word choice can be interpreted as talking liek a politician LOL.

    I’ll work on more of that questionnaire tonight. If I don’t get it completed tonight I’ll keep going until it is. A couple of the questions have me stumped.

    #855156 Reply

    I think the dress ones are good, but the casual ones still look too “old.”

    Something like this looks better to me.


    #855180 Reply

    Kate is right on the shoes she found,they are better,more casual and stylish. This whole “shoe thing” reminds me of an old Far Side cartoon. A woman is on a coffee date with a guy. She tells him ” I judge a man by the shoes he wears Jerry”. Underneath the table you can see his giant shoes decorated with bunnies,fruit and horns etc. It is funny and so true! Woman do look at something like a man’s shoes and rightly or wrongly make judgments/assumptions.

    #855203 Reply

    Having no preference isn’t interesting or exciting and doesn’t tell me who you are, Robert.
    All of your profile text needs overhaul. You need to remove the wishy washy language, regardless of whether if it’s true and try to sum yourself up. Please don’t call yourself a hopeless romantic. That brings to mind stalker tendencies.

    The thing is, you don’t seem to be very easygoing or casual with anything, either way. You are pretty particular about what you want in a relationship and what you’ll do in a relationship, right?

    Ideal date- going to a romantic restaurant and then an activity that we both mutually enjoy.

    What makes a restaurant romantic? Do you mean an upscale restaurant? Putting the word “romantic” in adds pressure to a woman who’s just trying to get to know you.

    What is an activity that you’ll both mutually enjoy? Can you choose one for your profile? The way it’s worded, the junior high school comedian in me thinks you’re talking about sex.

    Isn’t your ideal date more like:

    Going out to see the Christmas parade and tree lighting, followed by a sleigh ride and a bonfire with hot chocolate. I love the holidays!

    I kind of wish you’d just lead with the truth, that you are crazy about the holidays and you’re hoping to meet someone with a thirst for all things Christmas. Something funny and light. Name all eight reindeer and I’ll buy your first cup of cocoa/cider/drink.

    Not lists of date activities you’d be okay with.

    #855204 Reply

    Something to think about Robert. You’ve been alone for years. During those years you’ve learned to fill your time with meaningful activities. If you had been dating during that time you wouldn’t have needed to lean on your activities so heavily. If you end up in a relationship you may not need as many light shows or as many parades because the partner in your life will be even more meaningful and fun than those activities. You will still enjoy those activities and still want to do them but likely won’t need to do them to the extent that you do now. The time spent on those and other activities has probably actually hindered your ability to date and helped to increase your loneliness. You spend lots of time on your interests but it has still left a big gap in your life. Try to approach this from the other side. Fill the big emotional gap and then see how much room is left for activities. You will still get to do those fun things but almost certainly won’t spend the same amount of time on them and you probably won’t mind it either.

    #855206 Reply

    One thing to note about your pictures. When you are taking a picture outdoors using natural sunlight the sun should be angled to the side of your face. Don’t stare into the sun. It leaves you squinting and your eyes shaded so that they are hard to see. If the sun is at a 90 degree angle to your face the lighting on your face is much better and you don’t squint and your eyes are not shadowed. You do not want the sun in front of you or behind you.

    Choose your location because it has an interesting background and even then crop the picture.

    For current photos could you take one with fall/Halloween decorations. Around here our town square has been decorated with cornstalks and pumpkins. Some of the businesses have Halloween decorations out front. There is also a pumpkin stand just out of town with a large pumpkin display. Any of these would work for a fall photo. What do you have in your area that would work? A photo in a fall apple orchard might also work or a photo with bright orange and red maple trees in the background. Once Christmas decorations go up you could take some Christmas shots.

    If you like seasonal activities show yourself in seasonal photos.

    The picture of you in a suit has a vacant children’s playground in the background. You are essentially saying that you hang out at playgrounds while wearing a suit. Do you really want to say that you wear a suit to playgrounds and do you really want to indicate that you hang out at playgrounds? A grown man who hangs out at playgrounds tends to send a message of a man who likes children and I don’t mean that in a good way.

    Wear clothing that goes with the location. Dress up for a dressy spot and be casual in a casual spot. Unless you are a coach don’t show yourself hanging out at a playground.

    #855257 Reply

    Anonymousse: I am working with Wendy on a profile re-do. I just finished her questionnaire tonight. I’ll send it in tomorrow, I’m just taking one extra day in case I think of things to add, to make sure that what I am telling her is complete.

    Obviously, as you’ve seen, I am particular on some things, especially on core issues, or on certain “tradition” activities…I do seek the ideal but I am keeping in mind the community’s consensus that I may have to do something different, but I’ll deal with that if and when the day comes. Outside of the Holiday season there are maybe 10 things in 9 months that I look forward to. Other than that, it does not make much difference and would be happy with what she suggests. Problem is — and this has been a bit of a frustration of mine — that most of the women I have dated make no suggestions whatsoever and leave it up to me totally, so I never really get to learn which things she is *most* interested in.

    A romantic restaurant, at least to me, often does mean upscale, though I have been to some casual places, too, that I considered to be romantic. I did not interpret that question to mean ideal *first* date, but rather *any* date, even if we’ve been dating for two years. But I do see your point.

    In November / December, that would be the ideal date, but not January through October LOL. After the Holidays are over, I could just as easily go bowling, play pool, go to a movie, or watch a DVD at home. If I am with her, all are equally enjoyable to me.

    Skyblossom: I’ll keep those photography tips in mind.

    I hadn’t considered the background. I took photographs in parks, just because it is a public area without too many people around. Trying to take photographs of myself using the self-timer does not work where others are around. But I will consider the background in future photographs.

    I see your point about how I may feel about light shows when in a relationship, though that really started *in* dating. Any time I dated someone during the Holiday season the date was always a Holiday activity, so it is a part of who I am. But I do see your point that I am thinking about that in a backwards way.

    #855293 Reply

    So why not use the word upscale instead of romantic?

    The part I wrote with your “ideal date” is labeled ideal date in your google doc. And it is seasonally appropriate now/very soon. You can change it out after the season dies down.

    “If I am with her, all are equally enjoyable to me.”

    You don’t know that, though, Robert. Don’t over romanticize and fantasize about “her” just yet. This is where we’re getting the feeling that you are just inserting a woman into your fantasy of what a date or relationship is going to be like.

    You’re writing a profile to try and get ONE date. You need to write a profile that’s a little interesting and attractive and sounds fun. You need to step it up and be a little creative.

    What makes you special or interesting? Why would a single 40s ish woman want to go on a date with you? Even if you’d rather stay at home watching Netflix and cuddling in a perfect world, you should try and write something slightly more exciting and appealing to get one woman wanting to message you about your profile.

    #855294 Reply

    I’m really excited that Wendy is helping you, I can’t wait to read her profile or tips.

    #855297 Reply

    Oh man! This is great. I was so excited to get caught up this morning and see that Robert & Wendy are going to work together on this. I’m rooting so hard for you, Robert! Haha.

    The profile is already better, but I agree that it sounds wishy-washy (which is different from sounding easy-going). I think one of the problems is that you’re still trying to convey who you would be in a relationship or on a date, rather than who you are. What do you do for a living? After work to unwind? On weekends? Talk about those things.

    I disagree that a profile needs to be clever or witty (it doesn’t hurt if that’s who you are, but that was NEVER what made a profile stand out to me). The first thing I noticed was whether it was well written — never underestimate the value of good grammar and proper punctuation, folks! I liked profiles that gave me a sense of who a guy was and what he valued. I liked feeling like he was interesting and had a full life of his own. “I like to go out or stay in…” That’s not interesting, it tells me nothing about who you are or what you enjoy doing, and in the grand scheme of things, those are literally the only two options.

    The suit pic is the best of your pics, IMO!

    #855307 Reply
    Dear WendyDear Wendy

    Robert, don’t overthink this. The questionnaire should/could be answered in about an hour. I waited all weekend for your response and I’m still waiting! Come on!

    #855314 Reply

    I’m going to chime in with everyone else and say give us more of a sense of who you are! I’ve been online dating for close to a decade and a red flag for me is if the man doesn’t say anything about his career or job in his profile. 100% of the time, in my experience, that has meant he doesn’t HAVE a career or a job. That, for me, at my age, would give me pause and especially if the profile wasn’t otherwise compelling, would cause me to move on to the next one.

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