I happen to love 20 questions, but I get that many of you don’t– maybe you just need to think about it differently?  Don’t think of it as a chore, you need to view it as a game or like a treasure hunt, where each step of the way you pick up more clues about the other person.  What you are doing is actally called “mapping” in psychology, as you try to figure out (1) where someone came from; (2) where are they now; and (3) where are they heading?  This is why you ask some questions about the past, the present and then the future.  Easy!  Well, perhaps not for everyone…

My dad has the gift of gab and is super gregarious.  He was a bartender way back in the day, and worked on a cruise ship for many years, where he encountered people from every walk of life. Even today, he is quite the charmer, and I seem to have inherited that Casanova gene, so when I am playing 20 questions, it is clear that I’m not faking it– I am geniunely having fun trying to figure out the other person.  If you don’t feel this way, try to fake it until you make it!  As a witty friend of mine said recently, “you need to meet a lot of Richards to find a good Dick.”

While playing 20 questions, which should be an easy exchange of questions, with everyone taking an equal turn, maybe I should recap some basic dating guidelines:

1. Just Ask– Most women, even today, expect that if a guy is interested, he will ask her out.  We understand that we need to give you a green light signal, but many still think it’s up to the guy to then make the first move.  I disagree, but I may be in the minority.  Here is the deal- you just never know what the situation may be.  Good looking and intelligent men know they have their pick of the litter, so you may need to be a bit assertive to stand out.  Meanwhile pretty and smart women often scare off guys, who assume these women are already taken or will just say no.  But who knows? What is the harm in trying?  At the very least, a person should be flattered, and the best case is the person might say yes.  No decent individual will bite your head off.

2. First Dates– Guys need to show up on time, be nicely dressed, and at least offer to pick up the tab. Hopefully you will enjoy some witty banter, and try to close the date with a clear indication of what you want next.  Are you open to see each other again?  If so, great; if not, have a nice life, no hard feelings.  If you enjoyed your time together, then try to follow up with an email, text whatever, within 48 hours.

3. Avoid Making Excuses– For the longest time, I would use the “I’m really busy” excuse thinking that was polite, but guess what?  Guys are not stupid, and they can actually decipher our code.  It is so much better to just be honest and say, “I like you as a friend, but I don’t see us being romantically involved.”  Just be prepared for a come back like the one I got a few years back, where a guy said, “Thanks, I have enough friends.”  Alrighty then… good for you!

4. Don’t Forget to Keep Mapping– During the first few dates, as you try out different activities together, look to see if you are taking turns sharing the basic information you need when checking for compatability. It is not just about chemistry, which is key, but also do you connect when you talk about one another’s backgrounds- family, education, work experience, interests?

5. Pace Yourselves– There is no need to rush into anything– this is not a race.  It is good to space out your dates and take some time to process everything you are learning about one another.  Be sensitive to each person’s time constraints, other responsiblities, and the need for space and time in order to progress at a comfortable pace.  If someone is pushing up the timeline, you need to call them out on it– it really isn’t normal to expect to rank as a priority anytime soon in the life of someone you just met.  It is great to be excited, but curb your enthusiasm a bit– guys especially will appreciate this from women.

In the end, the best advice I can give for playing 20 questions is to be honest.  Nothing seems to drive people crazy more in the dating world than the feeling that they were misled.  No one likes to be part of a bait & switch scenario.  Why even try to play docile in the beginning if you know you are an alpha female?  If you are on a mission to get married, just own that fact, and don’t be upset if the other is not on the same page.  If you aren’t ready to commit to anything, just be upfront about that too– and try to understand that I may not want to be part of some a la carte menu.  If you like to be flirty, make that clear in the beginning– some will not be okay with that, but there are others who may agree to live with that as long as you leave the dance with the person you came with.  Remember, it takes 2 to tango– now go have fun finding that tango partner!

By Regina A. DeMeo, Esq.