You’re all settled in for your date, and that awkward moment arrives. What do you talk about? The key to a good conversation is to be prepared and know ahead of time what information you want to get from the conversation. I take a very systematic approach to this.
If you met online, prior to the date take the time to scrutinize your date’s online profile. Are there any inconsistencies? Is there anything that seems off, or maybe too general? Know what is in their profile inside and out, and be prepared to question them on things and have them expand upon what is written in their profile. For instance, does he have children? If so some questions you may want to address are when (or how often) he spends time with them. How does he spend that time with them? Is there a formal agreement to this arrangement? What are the children’s ages? If you do not have children of your own, remember this will be a huge lifestyle change for you.
What are his hobbies? Many men (and this absolutely drives me crazy) list every sport out there as hobbies, and nothing else. Really? They have no other interests? I personally would steer clear of these guys, but I know there are many women out there who are interested in sports. When evaluating what they like to do in thier free time, you need to know what it is you are looking for from a partner in this area. Are you looking for someone to do things with all the time, or do you already know you will want time apart to seek your own interests? Take all of this into consideration when evaluating how he spends his free time. Maybe there are things you would like to learn that he does regularly – this could be an opportunity to do that!
They key here is to ask! Have a conversation and learn what it is you need to know about him. Do not make it an interview and blast him with questions, but work these things into normal conversation! while you are chatting, you will also want to take note of what type of personality he has. Is he a “take charge” kind of guy who just automatically steps in and takes control of a situation, or is he more laid back? What is your personality (honestly, and not what you would like it to be)? Do your personalities work well together? How about his every level? Are your energy levels compatible? These are just some of many, many things you should look for on a first date.
The point is to make sure you do your homework ahead of time and be ready to find out the key information you want to know. In this age of online dating, you get one shot to make a good impression AND learn about your date. If you are lucky enough to have a date that did not originate online, you still want to find out as much as you can about him. If you met through a friend, drill your friend for as much information as you can get. Keep in mind that when information comes from another person, it may be skewed from the other person’s perspective. Just take note of what is being said, and ask your date about it later. If you met out somewhere and do not really know much about him, make a mental note of things you definitely need to know in order to proceed with a relationship, and make sure you find these things out. Either way, conversation is key on the first date, so make sure you choose the right location. Most importantly, remember this is not an interview – enjoy the date! Smile, laugh, and have fun!
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It is hard enough dating without any additional pressures and stresses. First dates are even harder. One of my rules, is that I do NOT want to kiss a complete stranger on a first date! No way, no how! I do not know enough about someone I just met to be any form of intimate with them, and that includes kissing. First off, I do not know his oral hygiene, which is super important. Second, gum disease is a bacterial infection and can be spread person to person via saliva. I know this is not sexy, but it is fact, and I think about these things, as should you!
Some people prefer a more active date than dinner, brunch, or coffee. There are plenty of things to do on a first date that are also great for getting to know someone. The first option is to go to a park, garden, or other recreation area for a stroll. In this environment, you have the opportunity to talk and get to know each other without having to stare at each other across a table. If you both like horticulture, go to a garden and enjoy that while getting to know each other. I will put out a few cautions here, though. If you do choose something like this and you have never met the person before, make sure you are going to a place that there are other people and you feel safe. Do not go for a walk on secluded paths, such as hiking, until you know the person you are with. While this should go without saying, sometimes when we communicate online, we feel like we know the person a little – WE DON’T. Stop for ice cream or a frosty drink on a hot day and enjoy that while chatting.
By the time we reach our 40’s, most of us are fairly set in our ways. We have lived full lives and experienced many things, both good and bad. Dating at this stage in life and beyond can pose some interesting challenges as we try to blend lives together that were very set by themselves. When I am evaluating a man, I think a lot about 





