Have found a possible match on one of the online senior dating sites and ready for your first date? And if you have already told this to your best friend or a close family member, then you must be getting bits of advice for what not to ask or not to do to avoid making a mess in your could-be relationship. If you are fed up such advice and wondering about what should be asked to kick starts your relationship with a bang, then this article is a must for you.

As an online dating expert, I am going to list a few questions that all older women and men eyeing love across the table should definitely try:

1. What makes him/her laugh?

At this stage of life where you have experienced almost everything, what you need is someone who can bring levity and liveliness to your life? Therefore, asking about the things or people who makes them smile is a good idea to start your conversation. This will help you to know about that person’s sense of humor along with his/her outlook on life.

Moreover, if you are already drooling over that person, then this will help you to impress him/her by cracking such jokes or talking about her favorite comedian. It will surely create a comfy zone for both of you.

2. Ask about the dreams or life goals

We all have that one dream we have never been able to fulfill. Therefore, ask if the person has a dream or goal in life. This will help you know if your dreams are compatible or not. Moreover, you can also have an insight into his/her value system. You can ask about his/her bucket list.


3. What do weekends look like?

The best way to know about a person is to ask about their lifestyle or what they do in their free time. If the person works on his/her day off, then you can guess that he/she is career-oriented or workaholic. On the other hand, if he/she tells you about going to almost every restaurant or club in the city, then you can understand that he/she is a party animal. Similarly, there could be many other interests one can tell you to let you have an idea of the compatibility between you two.

4. Who fascinate him/her the most?

We all have role models we want to become like. Ask about the same to the person to know what qualities he/she looks into a person.

5. Ask about the best meal he/she has ever had

Go more specific about this and you might get to listen to an entertaining story about food and travel. Also, when people talk about their best thing, they get completely involved in the conversation, which will be beneficial for you.
You may also add a few more questions to women seeking men or vice-versa, but always remember to go like you are peeling off an onion. Moreover, don’t force the person to answer your questions. Observe his/her gestures and you will automatically get to know if the person is comfortable with that question or not. Hope these questions will help you be an ice-breaker.

I would like to add that there are 3 Things Seniors Can Do to Meet Other Seniors


A more adventurous way to meet others is to sign up to take a trip—either with a local travel company that offers day trips or with organizations that specialize in trips for those 55 and older.

If you’re fit and active, and you enjoy rowing and hiking, there are organizations specializing in more active outings (such as Row Adventures) and more rugged adventures for travelers 55 and older.

Join a Senior Dating Site

Single and ready to mingle? Today’s 50+ dating sites can be great ways to meet seniors – even if you are not interested in beginning a relationship. Our Time is one such site, but there are others. Once you create an online profile, you have the opportunity meet others online before committing to meeting them in real life.