Thursday, July 23, 2020

Odds of Being “Chatted up”

Playing the Percentages
By Jeanine Williams
Stana asked her readers in her June 25 post to respond to Paula’s question about those of us who have been approached by men and what the results were, so I thought I would share some of my experiences as a T-girl who is out and about almost as much as Stana.
In the beginning, I used to avoid men as much as possible and if I entered a restaurant or bar by myself (which was uncommon) I would choose a seat that was as far away as I could as I was still trying to let my inner girl out and develop my confidence in public settings. 
As I became more assured of myself I didn’t worry about being read or passing (I don’t consider myself passable, but have found that I do blend in and people usually don’t take notice of me). I will sit where there is an open seat with the hope that another woman will be nearby to chat with. 
However, I have been chatted up by quite a few men and have had very few negative experiences. In fact, most have been pleasant and rewarding encounters and provided me with feelings of empowerment and affirmation of my feminine essence and energy. I’m reluctant to say “validation,” but I suppose that could be considered as well by some in our community who are seeking it that way. Personally, I’m not seeking too much “validation,” but have been more open to allowing myself harmless opportunities to express my femininity.
Before I describe some of my experiences with a bit more detail, I have figured out that men tend to fall into the following categories and percentages (Disclaimer: this is based on my experiences, yours may be quite different and certainly valid). I’ve found that 50% of men are oblivious to us; they are going about their lives, may or may not be enlightened about the transgender community and are not looking to meet women – most don’t present a threat but some may and we must, of course, be careful. That leaves 50% and they break down into 3 groups of about 17% each. 
The first group is men who have identified you as a woman (Woo Hoo!) and sit next to you or chat you up or otherwise indicate they are interested in meeting you. In my case, if the conversation goes past talking about the weather or whatever caused him to chat with me, I will then tell him “by the way, just so you know, I’m a transgender individual. I don’t try to deceive anyone.” (Or something similar depending on the encounter). At that point the alarm bells go off, the sheepish look appears on his face, a “umm, I didn’t know that, sorry to bother you, but hey it’s ok that you want to be you” or many other explanations including that “I’m only into real women,” so don’t be taken aback. Just smile and tell him to have a good day. Moreover, don’t be surprised if they just get up and leave; the rude ones will do that, whereas the gentleman may say, “Ok, thanks for telling me.” All of those responses have happened to me and only one was negative. 
So that means at least 67% of men are absolutely not going to be interested in meeting a transgender woman like you and me. So, on to the next group of 17 percenters.
The next group (#2) have figured it out. They have determined that we are T girls and are cool with it (some may be way to cool with it, so proceed with caution!). I have met quite a few men who fit in here and most of them identify as straight. They embrace the larger definition of femininity and appreciate the effort that we girls place on our appearances and demeanor. They will likely agree with the statement that, “transwomen are women.” 
I will admit that I have enjoyed meeting men like this; they provide an affirmation of who I am at that moment in my life. With that said, for the record, I’ve never gone beyond enjoying their company and compliments, but neither am I threatened by anything more significant than that. 
The man I’m sitting with at the recent Halloween event I attended (a “Tarts and Vicars” theme) falls into this category. He came with his wife and both were very accepting and aware of the transgender community. After his wife went to mingle, he affirmed that by asking, “Halloween costume or life style choice?” I was very honest and identified myself as transgender (I identify as gender fluid), got a compliment and we had a great conversation on many topics. He was not interested in me otherwise and I estimate that goes for the majority of men with whom I’ve interacted. Men like this are secure in their sense of self and are not threatened by people who are different, which I complimented him on – and he said, “thanks, you’re right.” 
On the flip side, this category very much includes the men who are attracted to you and may ask you out or be seeking a relationship. They will act and be motivated in the same way that most cisgender men interact with cisgender women. For them, you are a woman and they are attracted to the femininity you present. These men (as many men) are very visual – wear a nice outfit with heels, do up your hair and makeup and smile and these guys will be checking you out. 
In my case, I would say that 10 to 20 percent of the men I’ve chatted with were interested in me as a woman they would like to know better. These guys have given me opportunities to “get my girl on” so to speak and I admit that I have engaged in some mild flirting, which was fun for both of us.
I’ve had some very interesting and meaningful conversations with these men and have received my fair share of compliments. They were all polite, never did anything inappropriate, held the door for me, pulled out a chair, helped me with my coat and truly made me feel like a lady. There are several men I encountered more than once (like the manager of a bar that I go to for jazz night) who make a point of singling me out and asking how I’m doing and what I’m up to for the weekend.
I have told another bartender that when I’m sitting at his bar at the Sheraton in Duluth, that it’s like being on Free Parking on the Monopoly board. I’m in a safe place with a man who is totally cool with the trans community and can be myself without fear of going to Jail, paying rent or the luxury tax! I’ve been chatted up by quite a few guys at this bar and some know, some don’t and some spend more than a few moments thinking about it, and that brings me to the last group of 17 percenters.
These are the men who may have some degree of doubt about your gender identity. Maybe they want to get closer to confirm their suspicions or maybe they are interested and they overcome their hesitations because they see a woman they find attractive. I’ve had a few that will just come and stand next to me, some sit, some may say hello, but you can tell they are now trying to figure it out by the sidelong glances or the sound of my voice. It’s almost amusing, but you have to maintain your dignity and be ladylike. 
For me it eventually comes to a point that I let them know and then the outcomes can vary, but these are not like the men in group #1 who will be turned off – these guys will maintain some degree of interest and you can see them working through the news, of which they already may have figured out. I think many are working through the sexual orientation issues for themselves, “what does it mean if I don’t turn away or, what if someone I know sees me chatting up a man in a dress,” etc. It’s confusing for them!
I’ve had guys apologize and move on, or stay and chat for a bit so they don’t seem rude, or, and I think these are the most interesting encounters, some seem to come to an understanding with themselves that they are not gay, and they are talking with a woman, albeit a different kind of woman – and they eventually settle into chatting up the woman they found attractive! (Keep in mind the thumbs up ratio will increase if they’ve had a drink or two). 
I have used these opportunities to educate these men about our community during the course of our encounter and have had drinks bought for me as well. Hopefully, I’ve left them with something positive and have actually consoled a few who admitted an attraction to me and wondered why. I confirmed that they likely had very strong attractions to femininity and feminine energy and saw that in me and not to give it another thought. I said, “I consider myself a woman and it’s obvious you like women, so don’t beat yourself up” or some words to that effect. They usually feel better, say they were glad to meet me and we go our separate ways. 
Some of these men just want to talk with a woman. I was chatting with the manager of the jazz club I go to (who seems to fit in group #2), and when he had to leave, another guy moved right in and took advantage of the opportunity. He fit in group 3 – I think he knew, but he just wanted to talk and proceeded to tell me about his wife who had passed away and how difficult his relationship had been with her and I politely listened.
He seemed harmless enough, but I admit I was a tad uncomfortable with him because he stood rather close to me rather than sitting down and was quite tall, too. So, I wasn’t quite as charming as I usually am! I was glad when he left and then I struck up a conversation with another woman, which of course, lasted through closing time. 
My encounters with other woman are usually mutually beneficial and I’ve met with several on other occasions. It’s very comforting to be out and about with another woman or group of women and a lot more fun! Being around men can be tedious at times, but I have met several men who are interesting and enjoyed their company, too. 
I’ve always wondered if a guy I met, several years ago at the Sheraton knew – I never really had the opportunity to tell him because I was initially the third wheel in his conversation with the bartender, and when he went to serve another customer, I picked up where he left off and I never felt like I needed to say anything. I think that was one of the few times I would have accepted an offer to go and sit down privately and have a more meaningful talk. 
He was an attractive intelligent man with whom I felt entirely comfortable and he shared the conversation rather than dominating it. It did give me a bit of a flutter! Alas, we went our separate ways but he mentioned when he’d be in town again so that was yet another positive sign of approval. But for me, it was late April and that was the end of my feminine forays for my “girl seasons” – I went back in the closet til October. 
OK – so time to write about the times when the men I met were absolutely looking for more! I’ll start with the Oscar party that was held in a retro theater this past February. You can see more pictures – if you’re interested, Google then click on the first picture to see all the photos taken and see if you can figure out who my admirer was!
I wore this dress, which is just about the most incredible buy I’ve ever made, never thinking it would fit much less wear it out. Christmas shopping at a Walmart (please, no judgements) two years ago and this was hanging on a sale rack in the Juniors section for $9. So, what the heck, I bought it. Of course I need a corset, which I’m wearing – and I forgot my slim slip (which is why you can make out the outline from it), but it fits rather nicely, is clingy and sexy, but not overtly so and I added rhinestone earrings and bracelets. I received quite a few compliments from several women and the male hosts. 
I saw this guy making his way to me from the bar at the end of the party with two glasses of wine. He offers me one and the final “compliment” went something like this, “Jeanine you are absolutely gorgeous with great legs and if I wasn’t so drunk, I’d be all over you.” Well, alrighty then! Needless to say, I was so taken aback that I wasn’t able to respond right away, but eventually came up with, “Well, I guess I’ll just have to deal with that when you’re sober.” 
OK, girls, what would you have said and done? I will add that he was not threatening at all and actually was a very nice guy. I wasn’t offended and we spent about ten minutes talking during which he said something to the affect that “things are different now” to let me know that he knew and that “society is more accepting now of differences.” So he’s a keeper in group #2! I considered if he were sober, he would have been fun to flirt with to see what other compliments I could illicit, but I’d likely have kept my vanity in check - I guess! 
The professional photographer covering the event took this picture of me as well, just after Prince Charming graced me with his presence, so I thought I’d include it.
This was a fun event and I hope to go next year. This theater is welcoming to the trans community as is downtown Duluth in general. I’m looking forward to the re-opening of the Blackwater lounge this Fall (virus concerns permitting) as it’s my favorite place to go and listen to me friend Maxi Childs do jazz with her trio of men, who are also at ease with the transgender community. It’s always so nice for these guys to come up and say, “Hey, where have you been” and good to see you! The waitresses all wear black corsets and all of them seem to know what I like to drink, which is a chocolate martini – the glass alone just makes you feel sexy and the lighting is very conducive to passing. 
This is where, about four years ago, I was pretty much propositioned by a professor at the local university. That was interesting, but no harm done readers. His chat me up line (I was watching a basketball game) was, “So, do you have a horse in the race?” He was British and East Indian I believe. Chatted a few minutes, he settled in and I let him know my status, which didn’t seem to concern him and we talked for another 30 minutes or so. Nice enough, but other things on his mind and eventually my friend Maxi and her husband came by and rescued me from his clutches!
Here’s another example: I walked into the Blackwater one night a bit late, no tables empty except one with two bar stools and one man – so I asked if the seat was taken and he said no and waved me to sit down (I would never have done this 15-20 years ago). It was a good seat and Maxi, mid-song, waved to me as I took my chair. My companion then gave me the following compliment, “I don’t often see such tall regal looking women.” 
OK then, off to a good start, but I figured he may be in group #1 and didn’t know that this tall regal woman was not all she seemed to be. I was content to focus on Maxi, but he wanted to chat, so after the preliminaries, I let him know and he said, “Oh, ok. Well, it’s not like I was going to run my hand up your leg.” Uh huh! Sooo, once again I was at a loss for words and eventually managed to come up with, “Well, it’s not like that hasn’t happened before.” Yes, I know, what the hell was I thinking!
Anyway, a table for four with seat backs finally cleared. My new friend and I took it and about that time my friend Sue came to join me, so his possible advances ended and he excused himself about 15 minutes later. Therefore, he was placed into group #3. I’m sure he would have stayed if it was just me and him and I didn’t feel uncomfortable in his presence. I’ve accepted a few drink offers from men in similar circumstances, but have usually turned them down, particularly if I’m not sure of my surroundings.
Before I wrap this up, here’s a few more chat up encounters that I’ve had through the years. They vary depending on my level of confidence at the time they occurred. 
Many years ago, after I appeared with three other T-girls for a Denver radio show about our community, I went to the downtown Adam’s Mark hotel for a drink and to review my part of the interview. I was wearing my grey suit that I like to wear for professional presentations and, not to sound vain, I looked good. 
The bar was mostly empty and I was watching a World Series game when an older man walked in, took a look around, and quickly made his way to me. He pointed to his watch and then apologized for being late. To this day I feel badly because I just raised my eyebrows and sort of ignored him. He sat a few stools away and attempted to chat me up a few more times, but I was not very confident about engaging with men then, so I hardly spoke to him and he made a point of being disappointed and left. He obviously saw me as a woman and I suspect he would have been placed into group #1 when I told him, but who knows.
Recently, a bartender in Minneapolis, after chatting with him for an hour or so while he worked, said the following to me as he walked by me to serve another customer, “So, whose going to be taking you home tonight?” It was kind of a hit and run proposition!
After he came back my way, I said, “Regarding your last question, it’s still undecided!” Of course, I decided to go back to my hotel and left an hour or so later, but my last drink was on him so my “undecided” comment saved me a few dollars.
The creepiest contact I had was a guy who sat across from me at a bar in Minneapolis when I attended the Creating Change conference. After he asked if the seat in front of and facing me was taken he sat down and just stared at me. I asked if he was attending the conference and he shook his head (no) and I then let him know what the event was about and that I identified as transgender. He just nodded and softly said, “That’s OK.” I excused myself less than two minutes later with an “oh my” and a look at my watch!
As I look back on all my experiences though, I’ve had very few negatives. Most of the men seemed to enjoy being in my presence, indicated it was nice to meet me, the conversations were meaningful and I usually left feeling that I was accepted as a woman. A few men were disappointed that I wasn’t, but most were just fine with my identity and some obviously were seeking to become better acquainted. 
I’ve given that possibility some thought the last couple of years, but that’s likely the “road less travelled by” for me. Still, I’ve always been open-minded and if the circumstances were right, I wouldn’t rule out a romantic rendezvous with a man that I felt safe with. 
There is a provocative sultry side of my feminine spirit and soul where the femme fatale resonates, as I’m sure many of you can appreciate and I admit that it would be fun to let that part of my personality out (or, shall I say, “to let the Jeanine out of the bottle”). There should be no guilt here for those who share similar feelings; it’s just part of who we are and a part of embracing the woman within. For me, it would be kind of like taking a ride on the flume wave at Disney World – it could be a fun experience, but I wouldn’t spend all day in the park!
I hope my observations and experiences have been helpful. I wish all of you well in your respective journeys – for some of us, like me, it’s at the pace of a fast turtle. For others, the hare passed me by quite a while ago!
Remember, “Life can be amusing, if it’s treated like an adventure and not a chore!”

Source: Moda Operandi
Wearing Resort 21

Massimo Bellinzoni
Massimo Bellinzoni (right) femulating in the 1992 Italian film What A Night.


  1. AnonymousJuly 23, 2020

    Jeanine- Thank you so much for your post! I really loved the way you approached the writing, but moreso how you have handled everything in the varied situations! I can see how I'd handle (both well and not well) many of your experiences. Big hug, Sara

  2. hey Jeanine, I too have had a lot of dealings with men in my fem persona. All have been virtual experiences but the principles seem to be the same. We should make contact and chat sometime about men, lol

  3. AnonymousJuly 23, 2020

    Thanks for a great post!

  4. Wonderful article - informative and entertaining. You reminded me of my one and only "chat up" experience. At the bar at Applebee's one night after work. The gentleman (and I use the word intentionally) was obviously lonely and just wanted to talk with someone. He paid me a few compliments on my outfit and engaged in talk about the baseball game on the TV. As I left, he thanked me for talking and gently asked if he could give me a hug goodbye. I almost cried at this gesture, and gave him a hug. I floated out of there and back to my car.

  5. I've never hidden the fact that I'm a man in a dress, and don't think I could even if I wanted! Every now and then I've had conversations with men. A couple I've had in a "straight" location actually led me to believe the man talking to me would have liked to be in a dress, too! My first experience with the DC Meetup group was in a bar that had a bunch of "tranny-chasers" there with us. I was treated rudely and shortly after found out "the unwritten rules" were that the ladies who wished to be chased went to a certain part of the bar and those of us who weren't interested went to another.

    I've certainly gone to places on my own, but they were "safe" locations. I wear nice clothes and my natural hair can look really good, especially when I've had it done at a salon. My friend at MAC does a very nice job with my face, considering what I've given her to work with. I think most of my compliments are for giving it a good try! But being Mikki is the important thing, not getting hit on. I do it for the gender, not the sex.

    Let me toss in a couple negatives, too. Our Meetup group has opted for a more private location and no tranny-chasers are invited. Still, I've been hit on by two crossdressers who were there clearly to get laid. Both were rude to me, one getting a little aggressive. I just spoke up loudly and the organizers ushered her out.

    We know from experience that women, and those appearing to be women are more at risk. Add to that I'm going to be 79 in about a week and I have some mobility issues. I have to be extra careful out there -- and I am. Sharing this vulnerability with women has certainly increased my empathy with women, and I'm so glad to have had that happen. I'll still go out there, and can't wait for my stylist and MAC lady to be back in business. As usual, I'll be very watchful.

    Jeanine, I love your post, and those of my fellow ladies!

  6. AnonymousJuly 27, 2020

    Hello Ladies

    Very interesting experiences on being "Out and About". I would say that women tend to dress for the opposite sex when they choose to. This is when they wear high heels, a dress and or a skirt and blouse. Sure, they feel very feminine (I know I do) but they do this to show off their assets. I have great legs and I like to show them so I would be flattered if someone made mention of it. Does one feel feminine and sexy in baggy sweats and runners? I dont think so.

    The idea around sex is also interesting because if you are showing off assets in a environment where hook ups occur then you will attract men looking for sex. Men that chase gurls tend to do that at arranged events but innocent men in a casual bar may not read the situation right and then you get the ultimate compliment of being accepted as a woman.

    If you become "Good at it" then you are bound to be hit on by the opposite sex many times. How this is handled is where safety becomes very important.

    On a business trip in Montreal, I had gone out en femme to walk the cobbled streets and decided to go to the mall nearby first. I could feel the positive stares by some men as they checked me out in my heels as a business woman shopping after a day of work in the office tower in the mall. I also could sense the women who read me to be a fraud but at all times I always felt safe. I was just shopping by myself. You know that I am always hyper aware of everything when I am dressed because I think I pass well but if someone paid attention then I would be found out and then that could be a scary situation.

    When I dragged my aching feet back to the hotel (smart gurls carry flats in their handbag) and the doorman greeted me with a smile and a "madame" I felt good that maybe I could enjoy a glass of wine in the lobby bar and people watch.

    Well, a complimentary glass showed up with an invite to chat. Now I am scared as I dont have a fem voice. The man looked my way and I whispered "thank you" and he continued looking at his smartphone and I drank it quick, went to the ladies room and snuck out the back heading straight for the elevators with my heart racing out of fear and delight.

    As I soaked the day away taking a bath I reflected on how all women find themselves in the same situation every day and I only understand it for the time I spend out and about

    Be safe Be kind Mask up

    I am totally passable in a mask now. Not feeling sexy but feeling feminine

  7. AnonymousJuly 29, 2020

    Jeannie....nice article! So many points and experiences that we share. Over time, I had contacts with men that were in category #2 and 3 mostly. Personally, the more men that I came in contact with, the more comfortable I became as a woman, and the more I was treated that way. A number of CisWomen have helped me along the way as well.
    My experiences in the last 10 to 12 years makes me feel that you should have had a category #4....they could be called the " hunters and gatherers ". I will assume that no description is necessary.

    Be good to yourself.

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