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Thread: Go on a dinner date... me?

  1. #1
    Jennifer Wallace
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    Go on a dinner date... me?

    So I usually go out on Saturday nights to either a small bar or club that a lot of local TG's go to. I've known this one guy that I guess you'd say is an admirer and he seems harmless enough, although there is always (I sorry to say) something a bit off about these guys in my opinion. Anyway he sat with me last outing and really wants to take me out to a nice restaurant for dinner. Flattering sure, and I have to say I've never been on a real date with a guy. It would be fun to be treated well like this and I'm all for the female experience.
    So should I go? I'm concerned that he'd want something in return, and I guess concerned that he wouldn't as well if you get what I mean.
    Jennifer

  2. #2
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    Jennifer,
    Only you know this guy well enough to anwer this question , I guess you also know how you feel about a possible relationship so it's a case of being honest with yourself and the guy concerned .
    You don't say if he's TG or not and I also assume it's suppose to look like a male to female outing .

    Personally I'm OK with a social group outing but wouldn't possibly put myself in this one to one situation but that depends if the guy was a very old friend simply prepared to accept my TG status , if I felt he was looking for more then the outing wouldn't happen , that would be dishonest to both of us .
    Last edited by Teresa; 02-07-2019 at 02:56 PM.

  3. #3
    Silver Member Micki_Finn's Avatar
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    Well, do you actually have any attraction to men? Could you ever be in a relationship with one? If the answer is no, then it would be rude and disrespectful to lead this guy on and use him when there is no possibility of a relationship.

  4. #4
    🙊🙈🙉 Patience's Avatar
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    It really depends on what the fella really wants.

    If the outing is purely social, I don't see the harm in it, as long as everyone is open and honest about it.
    When haters hate, I celebrate!

  5. #5
    Aspiring Artist Kelly DeWinter's Avatar
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    Jennifer;

    If I were facing the issues you are facing at home, I would not. Is this something that would make things more difficult for you at home ?
    Kelly DeWinter
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  6. #6
    Platinum Member Beverley Sims's Avatar
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    You might have to meet up more often and then you can make a wiser decision.

    Get to know him and let him open up more.
    Work on your elegance,
    and beauty will follow.

  7. #7
    TrueNorth Strong & Fierce Princess Chantal's Avatar
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    You could accept his offer on the basis of it being going dutch so there is no stressful thoughts of owing

  8. #8
    Aspiring Member Joyce Swindell's Avatar
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    Did he say why he would like to do this? Is this an experience you would like to cross off your bucket list? I personally don't have that one on my bucket list. I agree with Chantal otherwise.

  9. #9
    Member Anne K's Avatar
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    As my therapist say,"Welcome to a woman's world!". Your concerns are justifiable and what every woman goes through as a relationship unfolds. You can meet the fellow at the restaurant and leave separately. It might be a good idea to take an Uber, rather than having to park away from the restaurant. When you arrive at the restaurant, be sure to locate the bathrooms. If he gets creepy, excuse yourself under the pretense of visiting the restroom, and walk out the door. If the evening goes well, do not leave the restaurant entrance until the Uber arrives. Handle Goodbyes how you feel is most appropriate,. That could be the fun part! Do not let him know where you live. Take it very slowly. Everybody wants love and companionship, but stay alert and develop a friendship before a relationship.

  10. #10
    AKA Lexi sometimes_miss's Avatar
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    Just tell him that sex is out of the question because you don't have a gay bone in your body, but if he wants to be friends you're just fine with that. If he sticks around, then proceed. Unless you want sex with him, in which case you're probably already good to go.
    Some causes of crossdressing you've probably never even considered: My TG biography at:http://www.crossdressers.com/forums/...=1#post1490560
    There's an addendum at post # 82 on that thread, too. It's about a ten minute read.
    Why don't we understand our desire to dress, behave and feel like a girl? Because from childhood, boys are told that the worst possible thing we can be, is a sissy. This feeling is so ingrained into our psyche, that we will suppress any thoughts that connect us to being or wanting to be feminine, even to the point of creating separate personalities to assign those female feelings into.

  11. #11
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    It could be a fun valuable learning experience.
    Just be sure you are both on same page .
    You are already getting to experience some
    of what women experience
    Take money enough for a cab ride home , tell
    a friend where you are going with whom
    Be sure you both understand you are just friends
    Behave like a lady
    And be home by 11


    JAS

  12. #12
    Platinum Member Crissy 107's Avatar
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    I think if you want to give it a try just be careful and like others have said have a plan to leave early if you need to. I also think letting a good friend you can trust know what you are doing and where you are going.
    Bottom line, you know this person, we don’t, so consider all the scenarios and proceed accordingly. Good luck and let us know how you do.
    Crissy

  13. #13
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    It's all about your confort level. It's 2019 and no normal man is expecting sex as payback for a meal. Now, he may be a perv who is expecting sex from the moment you say hello. That's a totally different story. Most men I have dated are actually a bit edgy as a result of the #MeToo movement. They will go out of their way not to do anything that could be perceived as offensive. One disappointing thing about a lot of "admirers" that I encounter is that they tend to be frustrated CDs who are trying to live vicariously through you (me). Sometimes they can be wonderful. Other times they start to ask a thousand questions that will make you think you were being interrogated by the Pink Haze Gestapo. Good luck!

    [SIZE=1]- - - Updated - - -[/SIZE]

    In terms of practical considerations, I find it useful to accept dates at places that aren't remote or hard to reach. I will often meet the person there or, if he is to pick me up, I will have my phone charged up and ready to hail a rideshare service (the big U or whatever is available in your area). It also helps to have some cash in this increasingly cashless society of ours, just in case. I have been on a ton of dates, including more than I'd like to admit with pervs and misfits, but I have yet to find myself in a scary or dangerous situation.

  14. #14
    Jennifer Wallace
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    Hi Micki, thanks yeah no I don’t really have attraction to men although I find it flattering that they find me attractive and I find that empowering you know. There would be no relationship so maybe best left alone. Anyway thinking....

    [SIZE=1]- - - Updated - - -[/SIZE]

    Thanks Monica, I think you’re on target about the admirer thing. I suspect he gets that something out of the deal. For sure he’s not my perfect companion choice but as I say I’d kinda of love the idea of being treated like a lady.
    As many point out my dilemma is that of any woman dating a fairly unknown man.

  15. #15
    Silver Member Devi SM's Avatar
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    I always say that there's so much wisdom in this web.
    I agree with almost everybody here but just one more comment, nothing is free in life, and everything has a price. We have said in Spanish , the curiosity killed the cat. Does it make sense?
    I tried so many things in life, especially on this enviroment and today I have regrets for things done. If I could repeat my life I'd never get in a date or something "friendly" if I don't have a real expectation with that man.
    It's very different to have a dinner with a friend than a dinner with someone that knows I'm a man dressed as a woman.
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  16. #16
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    We all are informed by our personal experiences. In my experience, I really enjoy being treated like a lady. I haven't had any problems with my approach to dating but I can understand why someone might be apprehensive. Best.

  17. #17
    Senior Member Jean 103's Avatar
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    No , you should not.

    Be real, your not intrested in men and you met in a bar.

    Me , I would go if I liked him. But I'm BI, and have been with men.

  18. #18
    Female Illusionist! docrobbysherry's Avatar
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    Jenn, u know him in the sense that u r both regulars. That means he should be safe enuff. However, honestly is the best policy! I know a number of girls that were wined and dined and even got plane tickets and rooms paid for by guys wanting to flaunt them in public together!

    Just tell him no matter what, nothing will happen afterwards!
    U can't keep doing the same things over and over and expect to enjoy life to the max. When u try new things, even if they r out of your comfort zone, u may experience new excitement and growth that u never expected.

    Challenge yourself and pursue your passions! When your life clock runs out, you'll have few or NO REGRETS!

  19. #19
    Aspiring Member Leelou's Avatar
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    Hi Jennifer, I would go myself if I had "the talk" with him beforehand. I saw your follow up post indicating that you don't really have an attraction to men. So I'd tell him that. It sounds like you'll see him again before the date is arranged. So that would be the time to tell him that you're a straight crossdresser. He might be OK with that.

    I'd say it's a definite plus that you have not just met him for the first time.

  20. #20
    Jennifer Wallace
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    Hi Jean, thanks for the input but are you saying if you’re not willing to have sex with a man you shouldn’t accept a dinner date? I assume since he asked me that he may be lonely and want a date. You may be correct and that’s my worry. I think it’s best I have a heart to heart with him before plans are made.
    Thanks to all. Jennifer

  21. #21
    Another fine dress AngelaYVR's Avatar
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    I’ve heard horror stories from women who felt sorry for guys and ended up being stalked and in terrible situations. Let sleeping dogs lie.

  22. #22
    Senior Member TheHiddenMe's Avatar
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    I have a couple of thoughts.

    First, as Dee, I have asked GG's to have dinner with me and they have gladly accepted, knowing that there was no expectation of sex (I'm married, they were not). Even in pre-marriage days, asking for a date did not presume sex was on the table. He asked you to dinner. Just don't call it a "date", just dinner with a friend. Talk it over with him.

    Second, as to admirers. I have not met many, so I'm not an expert. I don't understand the attraction, but I'm not yicked out about them. Why? Because for some reason I like dressing like a woman. For some reason, admirers are attracted to men dressed like women. If I consider myself normal for wanting to dress like a woman, then someone who is attracted to men dressed as a woman is normal too.

    I would be inclined to say yes if I had such an offer for a dinner out, assuming the man knew I wasn't interested in sex, and I had a reasonable assumption he was a decent guy.

    The same rules would apply if the admirer was a woman.

  23. #23
    Silver Member
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    It is 2019, most men are going to expect something afterward. If not the first date, the second or third. (Yes there are exceptions but that is the current culture today, even more so in trans chaser culture.)

    If you are not interested in men sexually, don't do it.

  24. #24
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    I feel a dinner a dinner date is just that nothing else
    No real pressure for anything else
    Force of any kind being considered assault

    JAS

  25. #25
    tiptoeing thru the tulips ellbee's Avatar
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    OMG, you're thinking too much. Just go!


    And why do I say this...?

    Quote Originally Posted by Jenniferx View Post
    ...I'm all for the female experience.
    There's your answer right there.


    You know, it's not like you'll now have to marry this guy, or even have a relationship and/or sex with him.

    You want the experience? Then go have it! And here's your opportunity. Not complicated.



    Years ago, I had a fling with a guy (with me always en-femme). Long story, won't go into it now (already have here in the past).

    We hung out at his home. We had public "dates"... And yeah, we had sex on more than one occasion.


    Am I attracted to guys, per se? Not especially. But it's something I wanted to do... And so, I did it!

    No regrets here, either. It was all quite the experience.


    Would I do it again? Nope!

    But that doesn't mean that I didn't have a great time, either.


    Honestly? If I hadn't done so, I'd still be wondering to this day. And probably kicking myself that I had "chickened out."


    Want the female experience? Then use your women's intuition to see if this is something right for you, at this time, with this guy.

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