Thursday, June 25, 2020

Chat Me Up

Paula wrote, “As one woman to another, and excuse me if this is a silly question, but why don't more girls write to you about being approached by men... and enjoying it. It has happened to me twice recently and I was absolutely flattered. I think it is the ultimate compliment.”

I don’t know why more girls don’t write to me about being approached by men.

I have had numerous men check me out and that in itself is a compliment. But I have never had a man take the next step and chat me up. Have you?

If you have been approached by a man, how did it go? How did you handle it? How did it end?

Inqueering minds want to know, so comment below about your close encounters with men. Or send me your stories via e-mail (click on the “send me e-mail” link below my photo in the sidebar.

I’m all ears.

Source: Bebe
Wearing Bebe

Femulating in the mid-20th Century
Femulating in the mid-20th Century


  1. Only twice have I been approached by a man - both were at gay bars. Both times I'm not sure if they were approaching Julie or if they were approaching a guy in a dress. Seriously, I am not interested in attracting men, but the compliment DOES give me quite a head rush.

  2. AnonymousJune 25, 2020

    I've always been extremely attracted to transgender women. When I was single, I would have been pleasantly surprised to find the woman I was chatting up was a femulator.

  3. Sally StoneJune 25, 2020

    I guess as socially active as I am, being approached by a man was inevitable. In fact, I have been the subject of a man’s interest on a few occasions, which surprises me, given the fact that it’s pretty easy to recognize I was not born a woman. Not a single one of my personal encounters was a case of mistaken identity, instead, it was obvious to me my suitors were attracted because of the unique kind of woman I am. Still, I have to admit that in each case, I was flattered by the attention.
    The latest encounter occurred last fall when I stopped by a favorite local restaurant and visited the bar for a glass of wine. The only seat available was a corner stool which had me seated across the corner from a gentleman nursing a beer. He wasted no time saying hello even as I settled into my seat. I am always the recipient of friendly greetings, so the hello didn’t surprise me, but I was taken aback when this particular gentleman continued beyond his greeting to a full-blown conversation.
    We exchanged names, talked about where we lived, what we did for a living and what kind of music we liked. Turns out, he was a connoisseur of classic rock and roll music and we ended up talking quite a bit about favorite bands, best guitarists and drummers and so on. It was mostly friendly small-talk until he suddenly asked me if I had a boyfriend. The question had me thinking a couple of things. Did he truly not know what kind of woman I was, or, since I was presenting as a woman, did he just assume, a guy who dresses like a woman must surely be into guys?
    Being married to a woman, I clearly didn’t have a boyfriend, and being married to a woman, obviously, I wasn’t into guys. Consequently, I just said that I was in a relationship, but didn’t go into details. Undeterred, he invited me to a local rock concert featuring a Pink Floyd tribute band. He explained that we could go simply as friends. I politely declined his invite thinking it would probably cause him to lose interest in me. It had been my experience from a previous encounter that once the man knew I wasn’t looking to hook up, he would quickly move on to someone else.
    With this gentleman though, he didn’t seem put off by my unwillingness to accept his invitation and we quickly went back to small talk. When he finally did get up to leave, he shook my hand, told it me it was very nice to have met me and he hoped we would meet again.
    After he left, I pondered his advances and wondered just what it was about me that had fueled his interest. I guess I’ll never really know, but whatever his motivations, it is nice to know that occasionally, my feminine presentation, garners attention beyond the obligatory hello.

  4. Years ago I used to meet a group of five or six people at a tavern I went to. Besides me, there was only one other LGBT person in the group. One of the most intriguing person to me was a beautiful long dark haired cis woman who was a beautician and a part time stripper. Along the way she and her boyfriend impulsively decided to get married.
    The marriage lasted a very short time and one night I went in there, her ex was broken up by the whole affair. As the evening went on, I was the only one who seemed to care about his feelings. He was a big bear of a guy who rode a classic motorcycle.
    From then on, he always would sit next to me at the bar and we would talk. He was the first man I ever thought I could get along with long term as a woman.
    Unfortunately, shortly after that, he changed jobs and left the area.
    I often wonder what would have happened if I had ever got an invitation to ride on the back of his motorcycle!

  5. The male interest I've drawn has always come from people in a bar where I'm watching a drag show. I have been approached by women in a public situation. It is nice to get unsolicited complements on my appearance. I'm a big ol' lady and I'm not sure which thing I enjoy the most -- the complement or the shock of surprise!

  6. I, too, am not interested in sex with men but have been approached a number of times - mostly in straight bars on Halloween. On those occasions, it was pretty clear I wasn't a real woman, but the men all would say, in some fashion or another, "I am not gay but I do have to say that you are a hot woman," or, I am not gay, but I'd definitely take you home and do you." (Had this comment many times!) While dancing with my friends, other guys would come up and dance sexually and suggestively with me. When En Femme in non-Halloween situations, I've had mostly my female friends say how hot I am and that I have very sexy, feminine legs. Other women I don't know have complimented my clothes, my style and other feminine attributions, but I never inquired whether they knew my real gender. I just thank them for my style and am appreciative of the affirmation I receive!

  7. AnonymousJune 25, 2020

    I am not sure that I would want to look good enough for a man to want to chat me up
    Things can turn very nasty when men realise that they are not chatting up a woman
    T girls have been killed when that happens

  8. As a performer, I kind of put myself out there, I suppose. I do try to present my more-glamorous self on stage, but not so much as a drag queen would. Still, it's an act, and I don't do it to attract anybody to anything but just that. I try to be entertaining, but I'm more hopeful that people will appreciate my music more than my stage persona. There are men who can't make that separation, though, and I've been hit on so many times that I can't even count them. I'll admit to feeling overwhelmed by what I perceived to be compliments the first few times, but I've mostly been creeped-out by the kind of attention many men have given me. I've even had to physically fight off groping hands.

    I came to the conclusion years ago that men who are interested in trans women will treat us differently than they would a cis woman. Not that they're necessarily perfect gentlemen with cis women, however. I think that they must believe we get all dolled up for the purpose of attracting a sexual partner. I don't have to be wearing a sequined evening gown in order to be approached, either. There have been many times when I have been approached while waiting for a bus after work. I was even stalked around the aisles of a Walgreen's one night. I was afraid to leave the store, for fear he would follow me into the parking lot. When he finally did approach me, he asked me if he could buy me a drink. I told him that I needed to get home before someone started wondering where I was. He finally gave up on me and went to the check stand, where he bought a bottle of whiskey. I thought: Oh great, he was expecting me to go out in the alley to trade swigs until I was drunk enough to submit to his wishes.

    Enjoy the attention, if you will, but be careful. Chances are, you are being objectified more than anything else. Me Too can apply to us, too.

  9. AnonymousJune 25, 2020

    I have had a number of positive experiences from women while shopping.
    Remarkably, never have I had any notable negative pushback whilst 'enfemme'.
    I was approached by a woman who was so impressed with my clothing and makeup, she wanted me to help with her upcoming wedding! I politely declined.
    More than a few ladies have approached me, asking for my advise on the item they had just picked. I am quite flattered by their inquiries, and do my best in their best interests.
    One elderly lady approached me in the checkout line to let me know that
    less than a mile away there was a yard sale where there was a huge selection of clip-on style earrings, as she noticed that I was wearing clip-ons. I would have gone to the yard sale, but our CD/TG meeting was just minutes away. I dont believe she had a clue to the fact I was not a woman....
    As I exited the local Belks department store a lady complimented me on my outfit of a layered flowing, billowing, calf length purple skirt and lavender floral blouse, (with white pump (heeled) sandals. 'Where did you get that lovely outfit?'. I replied that "I got the whole outfit from Value Village, a thrift store".
    If you have not read my 'chivalry' encounter, please do.
    Have Fun! Be Safe.

  10. When I go out dressed I just want to enjoy the experience, and try to blend in and be “invisible”, and dress accordingly. I know I am not a beautiful woman, nor do I ever try to be one. On the few occasions that men showed interest in me I felt uncomfortable and not flattered at all. On the other hand, I did feel flattered twice when it was cisgender women who seemed to be attracted to me.
    Anna María

  11. I’ve been asked out by men, during the day in various situations, four times. Each time I am extremely flattered but feel bad for them as they are barking up the wrong tree! But I do admire their gumption for asking and respect that they acted as gentlemen about it in contrast to the more frequent passive aggressive techniques of the typical chaser. A lot of guys seriously need some dating advice! Off topic but I find that women are just as interested in us as the men!

  12. AnonymousJune 28, 2020

    While out in Portland, OR, a woman approached me to ask where I got my skirt. My girlfriend thinks the woman didn’t clock me until I spoke.

    While out at home, we went to a kinky art showing and I was dressed andro - tight ripped crop jeans, ankle booties, stripped shirt and motorcycle jacket, but no wig and light makeup. A man complimented my boots. My girlfriend rolled her eyes and said “Really, I can’t take you anywhere.”

  13. StephanieJune 29, 2020

    I'd been shopping in Pasadena in a cute business skirt suit and sky high heels, and ducked into an Old Town restaurant for dinner and a cocktail. A cute man several tables away waited until I was finished. We exited together and he struck up a conversation as we strolled. He invited me to join him for another cocktail together or trade numbers. It was the first time I was captivated by a man politely hitting on me and I wasn't quite prepared for it. Feeling tired, I declined.
    Since then I have been prepared, and have been ready to say yes. A local bartender and two men on staff at the Pasadena Whole Foods market made advances that were adorable. Two of the three got my number, but they both sort of self destructed via text before we could be social. Weird.
    My psychiatrist once said, "Most men who want to date trans women have trans leanings themselves." I suspect he's right, as even dogs get confused when they finally catch their car.
    I've since dated several very sweet men I met through OK Cupid online.