First Date in 10 Years? 6 Questions To Ask And 5 Things You Must Do.

First Date in 10 Years. What do I do?

Dear Tracy, I’ve had a steady boyfriend for the last 10 years. We’ve broken up and now I have a problem. I haven’t been on a date in so long but my roommate set me up with a guy she knows from work and after reading your letter earlier today I realized how much I don’t know about dating and I’m scared to death. What specifically would you ask a guy on a first date, that you think I need to know?



Every person is different. What I would want to know wouldn’t be the same as what you would want to know, because every person is different and we have different likes and dislikes. But if it were me on a first date, here are some questions I would ask him.


Before getting to these questions it is important that it certainly depends upon your consideration of what you wanted to do and what you want to ask on your first date in 10 years. 


6 Questions To Ask On Your First Date In 10 Years



1. Treat It Like a Job Interview:


I would treat my first date with some guy I didn’t know anything about, like a job interview. I would ask specific questions that would help me get to know him and see if he was right for me. Family is important to me, so I would be sure to ask if he was close to his family and had any siblings. As a person who comes from a big family, I have found guys who have no brothers are sisters and tend to not get along so well with my sisters and me.


2. Ask Him About His Past Dating Experiences:


I would ask him the one thing he wants me to know about him. I would ask him the reason he broke up with his ex-girlfriend. I would ask if he goes on a lot of dates. This will let me know if he’s a casual dater, something I’m not looking for. Now that may not be an issue for you, but for me, it is.

3. Ask Him About His Taste In Music & Art:


I would ask what kind of music he likes. If he loves rap, well, then I know our tastes are very different in music, and that wouldn’t work out so well long term as I detest it. I would ask what kind of tv shows he watches because then I would know if he’s a serious drama kind of guy or really what his humor level is.


4. Ask Him About His Ambitions:


I would ask him about his job but focus more on his lifelong goals and aspirations. If his long-term goal is to marry 17 women and quit his job, then this probably isn’t the guy for me. A man with a strong ambition and commitment to his dream must consider because such men put all their efforts into making your relationship work. 


5. Ask Him About His Expectations:


I would probably ask him about other personal things like what he’s looking for in a woman, such as the ability to cook and clean or a career-minded person. If he wants a domestic goddess, I know he’s not right for me. I would also ask the question I said before: What is the pickiest thing you ever broke up with a girl over? This is important because what if it’s something you do all the time? It will also help you get to know if he’s anal retentive about really stupid stuff.


6. Ask Him About His Social Circle:


I would probably spend some time on questions about his friends too. I would want to know things like if I lined up all of his friends right now out of the group, would he be the funny one, the serious one, the slob, te, he nfreeat ak, the workaholic, and so on?


Just Keep It Honest:


If you are still nervous, write down about 30 questions and then memorize them. Also, it might help to have a joke to break the ice. Even a stupid one, like I heard the stupidest joke at work today. Some lady went to the doctor and said she broke her arm in two places. The doctor replies quite seriously, then my advice is you stay out of those places.


Let’s face it, first dates are tough, and the majority will end before they even really start. Here is a list of the five most important things men and women should remember.


A first date is simply two people getting together to find out more about each other. It’s an interview where you determine if the other person will be a good fit for you. Many of these things may seem like common sense, but you will be surprised by what some people can do.


5 Things To Do On Your First Date In 10 Years


When you want to be in a relationship after a long time you have to be precise in what you do to the person you are meeting. So we have gathered six things that a man and a woman must do when they date after a long period of time. 


Top Five Things for Women

  1. Say thank you if he does something nice and/or unusual.
  2. If you’re not interested and rather be friends, just say it. The guy may not want to hear it but trust me, it’s better (and easier) now than later on.
  3. Don’t get drunk (see #3 for men).
  4. Laugh at his jokes, even if they are awful.
  5. Make lots of eye contact and smile.

Top Five Things for Men

  1. Listen to your date. Listening to your date is not the same thing as waiting for her to pause so that you can begin speaking).
  2. Be chivalrous…yes that means you’ll have to open the car door for them.
  3. Don’t get drunk. If you’re not sure you can, just stay away from alcohol altogether.
  4. Always be on time.
  5. Play it safe and stay away from religious and/or political topics…this can lead to disaster.


You can always try things you like and do things you like. People like people who just be honest and open to them. So try to be open and real with all you do in your first meeting. 


It’s Never Too Late


It is never too late to be in a relationship. Just enjoy your life and your moments. Be nice to the person you are meeting and be open about yourself if you feel comfortable doing it. It is surely your call to decide whether he is the right one you were seeking and does he deserve to know what you intended to tell him.

author avatar
Tracy Tegan
Tracy Tegan has spent the last seventeen years as a professional blogger about relationships, dating, and issues pertaining to gender equality at In her spare time, she writes romance novels that are available at Amazon.  You can check out Tracy Tegan's latest romance novel, Crescent Moon at Amazon.

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First Date in 10 Years? 6 Questions To Ask And 5 Things You Must Do.

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