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.
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 ?

[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....

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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.

[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.

[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.

[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."

[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

[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.

[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.

[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.

[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.

[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!

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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.

[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.

[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

[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!