Go on a dinner date... me?

[Jenniferx]

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.:o
Jennifer

[Teresa]

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 .

[Micki_Finn]

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.

[Patience]

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.

[Kelly DeWinter]

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 ?

[Beverley Sims]

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.

[Princess Chantal]

You could accept his offer on the basis of it being going dutch so there is no stressful thoughts of owing

[Joyce Swindell]

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.

[Anne K]

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.

[sometimes_miss]

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.

[Jean. Ann]

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

[Crissy 107]

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.

[MonicaPVD]

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!

- - - Updated - - -

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.

[Jenniferx]

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....

- - - Updated - - -

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.

[Devi SM]

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.

[MonicaPVD]

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.

[Jean 103]

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.

[docrobbysherry]

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!:brolleyes:

[Leelou]

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.

[Jenniferx]

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

[AngelaYVR]

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.

[TheHiddenMe]

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.

[Vickie_CDTV]

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.

[Jean. Ann]

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

[ellbee]

OMG, you're thinking too much. Just go! :roflmao:


And why do I say this...?


...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. :heehee:



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! :p

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. :)

[TheHiddenMe]

What ellbee said. 1000%.

[GretchenM]

I lean a bit toward what Ellbee has argued. It is a situation where you can experience a new dimension in your womanliness.

However, like most everybody else, I recommend you be super careful. "Tranny chasers" are out there and they can be very subtle. Even little hints of expectations can be quite meaningful as to his motivations. Not only words, but facial expressions and other body language hints. Women are really good at picking up those signs, but you are not a GG. Many women today are more assertive than in the past and will say outright what the boundaries are. Also, remember that he could artfully spike your drink with a drug. Not trying to make paranoid, but just pointing out that a good deal of caution should be exercised. Around here there is a saying about being safe. "Do what a GG would do and double it."

[Sherrii]

I mostly go along with the good advise you have already received and will just confirm that you want him to know how you feel and what you expect and don't expect up front. If he knows how you are feeling and still wants to do a "date" well if you are careful, why not? Sherrii

[deebra]

GO, meet him in the lobby and then walk into the restaurant together. Your chance to see how it feels to be treated like a lady.

[Cheryl T]

If you are interested in the date and the experience then go.
Just make clear to him that your acceptance is not an indication that you want anything beyond the date.
Don't lead him to believe that anything else will occur, unless you want that.

[Denise S]

I would say go. Deep down you must want to go out on a date since your asking all of us. As all the other girls have said be and have fun.

[Krisi]

There was a post about "issues at home". Are you married? If so, Do Not go out on a date with a man. This will come back to haunt you and it's cheating.

If you're not married, then it's up to you but I suspect that a guy willing to spend money on you is expecting something in return and that something is sexual. Are you willing to have sex with him? Give him a BJ?

Remember just because you dress as a woman, that doesn't make you one. In reality, you are a man having sex with another man. Not that there's anything wrong with that as long as you understand what you are doing.

Nobody here can tell you what to do or give you permission to do something. We can give you things to think about but in the end, it's your decision and it's you who has to live with that decision.

[Jenniferx]

So if going to dinner with a guy cross dressed is cheating, perhaps going to the bar and having a drink that is paid for is cheating too? Is it that my wife doesn't approve that makes this cheating? Then the bar is out, meeting friends is out, being "Jennifer" is out because all of that she certainly would not approve of. And here I spent all that money on therapy and I only needed to come to this forum- doc: just because you dress like a woman doesn't mean you are one- and our time is up. Maybe it's just me but it seems so unenlightened to assume that going to dinner suggests some sexual payback, but that was the advice and knowledge feedback I was looking for (not a judgement of my home life). As you say in the end it's my decision and thanks to all that offered advice

[Diane Taylor]

What have you got to lose? It might be fun. Just go to an upscale place and let someone know where you are in case he turns out to be some kind of jerk. There doesn't have to be a second date. I kind of share your feelings regarding "admirers" because there were a few times when an admirer wanted to take me out and I politely said no thank you. I'm sure they'll want something either that night or soon after. One time I went on a dinner date with a gay co-worker who had no romantic or sexual interest in a T-girl. He was the kind that are referred to as "straight acting" and we looked pretty much like a hetero couple. We had a great time.

[Zoeytgtx]

What have you got to lose? Personally, anything that expands the envelope to see the world from the female perspective is enlightening. I did it a few times and the guy honestly enjoyed it just being seen out with me as a hetero couple.

[Stephanie47]

You said "There is always something a bit off about these guys in my opinion." Maybe that answers your question. I read in a January post you gave an admirer several kisses. Same man? Same persistent man? Perhaps this will go too far down the road and you end up losing control of the situation as so many women lose control. A number of years ago you posted your wife was not in the least supportive, and, your son "hates" it. How would that sort of encounter go over with your wife? I don't think for a minute my wife would find this "harmless." My wife would call it "cheating." If marital status is no longer an issue I'd keep it in mind many women started out on an innocent date which then went in a direction they did not anticipate.

[kimdl93]

Probably not... particularly if your sexual orientation is heterosexual.

[Maria in heels]

I think that you definitely should be open and honest with him BEFORE you agree to dinner. Maybe he just wants to talk with you alone, away from the noise and crowd of a bar, and nothing more. On the other hand, as some have said, the cues are there and you know that he is or he isn't hinting at something more than just chatting. Does he make the jokes about being intimate thru the phrases that instantly trigger the "yuk" inside of you? If so, then dinner is probably not a good idea. Just ask him straight out and let him know that you don't want to mislead and we can have dinner as friends but thats all, unless you want something otherwise..

[Eemz]

Hey Jennifer. I say go for it. If you're not cheating on anyone then what have to got to lose? You're not marrying him! You're just going to have dinner and talk without all the big group around and get to know each other a bit better. If you like it, you'll do it again. If you don't you won't. Simple.

If sex is definitely not on the cards, then ok you might want to make that clear up front before the day. If nothing else, to avoid anyone embarrassing themselves by misreading "the signs" and then everyone is all awkward and the night is ruined.

I've been to dinner a couple of times with a gay male friend. People think we're a hetero couple (we're not any kind of couple). He doesn't care and it's been a really nice experience for me.

[girlyman1977]

Lay the ground rules before hand so there arent any suprises later. As long as he knows the deal he cant say well you led me on after the fact.

I know the frustrations of the "game". Just had a girl at this convention that I was doing the AV for give me subtle hints that she was interested. She was my contact for the group. She had no ring on so I was thinking ok I am going to scout this out only to hear 2 minutes into our conversation about her husband.

Long story short just be honest and upfront and don't lead them on and it will be fine.

[helenejo]

Why not go for it.
If you are having a nice evening and one tging leads to another....it could be an even better night

[~Renee~]

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.

This sounds like good advice given the odd sense you have about him plus your own SO situation. As wonderful as the idea sounds to you; Jean, Vanessa, Gretchen, and Micki give you additional reasons to hold off. Paranoia is sometimes beneficial

[Krisi]

Jennifer, You asked for advice and I answered with mine just as many others did. You didn't put any conditions on the answers so I posted what I honestly felt was good advice. If you didn't agree with my post, fine. but there's no reason to get snarky about it. Just move on and take the advice that suits you.

Asking for advice on the Internet has the risk of hearing suggestions that you don't like. If you can't handle that, don't ask.

[Di]

Your title says Dinner date and you said they are an admirer.
So I’d say No.

As a GG , if a man invited me to dinner (unless he was someone that was a very close friend), I would assume I was being asked out on a date. Otherwise why would a man I barely know want to have dinner with me?
And

Is going on a date cheating if you are married? I don't know, you need to talk to the person you married.

So no judgement on your home life .....We are answering your question from our perspective . And if there is things in your home life ( you alluded) we just are answering our honest opinions so things do not get even more complicated in regards to your home life .
I think we try to give support and honest opinions.... surely you do not want fluff answers like go for it girl and such .
And like you said it’s your decision and it is .....just think about it from every side . I am a GG and I would consider a dinner date cheating.
Its a compliment YES but I’d steer clear.
Just my little ole advice