What would are appropriate questions to ask mature man while dating?

Question

I am interested in dating a man who is 55 years of age, he has his masters is recently retired and owns a consultant business. I will be 50 years of age have a high school diploma and currently still employed.

He has invited me to ask questions of him and for some unseen reason I am unable to ask questions of him. At times, he has mentioned he feels disappointed because he is interested in me and he no longer contacts me as often as once did. I do like this person and I do not want this person to lose all interest in me.

I have asked him the basic questions, if he ever married, do you have kids and pets, what are your likes and dislikes, and what do you like to do when he isn’t working. These are vague questions and I would like to ask him significant questions, and no other questions seem to come to mind to ask of him.

Answer 1

- The good thing about chemistry is that, you don't need to plan the conversation. If you two are into each other, the conversation will flow on it's own. Otherwise, I don't have any suggestions.

Answer 2

honey you have to second and third level probe,,
whenever he says something you have to ask him something else about what he just stated.
ie...."i never liked florida"
you....well why not?
him ... it rained too much.
you...well what cities did you visit
him...miami
you....hey maybe it was just the rainy season, florida is pretty long, did you ever visit any other city maybe further north
him...no
you...well you see, you cant judge, where else have you traveled too.
.... how was that
.....when i travel i look at the architecture and like to learn about the history of the .....
and i could go on and on,, these are conversation skills. you interject and ask . you obviously are boring to him because you have no conversation
ps,,, you want to get him a little rowled,,,,try to gear the conversation a little bit towards sex,, dont be raunchy,,,,,but sex is always a stimulating conversation.... as a matter of fact you could tell him what i have mentioned, see how he reacts and start probing with other questions or maybe things in your past

Answer 3

Have you ever asked him exactly what he does as a consultant? Ask him to explain the process that he goes through in making his decisions for those who consult him. Ask him to give you an example. Not only will you be showing an interest in what he does but will end up leaning something new.

Answer 4

Girl, you have to learn to turn the tables around. Why should you ask, tell him to ask you fun questions. I think conversations are better than Q's and A's. You are a women so you are smarter than him no matter what. lol Want to get him interested fast? Its a song; Lets talk about sex baby, lets talk about you and me... Look he is old and he wants to belong so you are not providing. he is longing for a feeling of belonging.. Well heck what do I know..I am not telling you to sleep with him but talk about it. He is not 20. So he just wants to hear about it.

Answer 5

Ask him how does he feel about you.

Ask him what he sees in the relationship the two of you currently have.

When two people are dating and liking each other regardless of age and educational background, I am pretty sure two people would like to know more about how each other feel about each other.

Less of course one party is not looking to be in a committed relationship.

Answer 6

It's hard when one person in a relationship is better educated, because, in your case, he has more to talk about.

You can ask what type of music he prefers, who his favorite artist is, what wild and crazy things he did in college, or better yet, ask him about stuff YOU are interested in....Photography? Politics? Nature?

You need to find some common ground or else your relationship will go stagnate, really quickly.

Answer 7

(Ask him) Biggest achievment/ Favorite memory/ First time in love/ Ultimate goal in life/ Ultimate dream in life/ Favorite subject in school(and why?) First kiss/ Favorite book/ How he feels about his family and what they are about/ How he feels about politics/ Religon/ Ancesstors/ Favorite wild animal(and why?) Stupidist mistake/ Best mistake/ Art/ Artist/ Actor/ Musician/ Dance/ Dancer/ Broken bones/ Favorite car/ Favorite city/ Best president/ Sports/ Biggest fear/ etc.etc. He wants you to get inside of his mind and make him think. Create scenarios and ask him "what would you do?" Then you have to remember his answers and treat him like you havent forgot them and you never will.. Sounds like he is genuine and doesnt want a woman thats to be with him for his money, cuz it sounds like he his loaded..GoodLuck...

Answer 8

Maybe take him to a museum, and you could discuss what he thinks and feels about the different pieces of art. You could also go to a movie together and ask his impression of it. You could always just discuss his opinions on todays current events.

Answer 9

Why don't you ask him about his job, where has he travelled or would like to travel, his family, his friends, if he has any goals he would like to accomplish and how he plans on accomplishing, ask him to tell you something he always wanted to do but has not yet done. Ask him about his life, his childhood, where he grew up, his politics, his favorite foods, foods he hates.

Once you two really start to converse, really listen to him. He'll give you clues about himself and you can just ask about details of things he has said.

Answer 10

Topics of interest - religion, current affairs, books. What are his long term aspirations? It appears that he needs to feel your depth more than he is/was. Hence the reduced contact.