Literally all sources of dating advice out there teach guys a similar strategy on making a conversation with a woman when they meet her or during the first date - and that strategy is asking her open-ended questions about herself. However, this turns into one of the most common mistakes that people make on first dates that makes them come across as very boring and predictable. Asking cliche questions one after the other such as “Where are you from?” “Where did you go to school?” “How many siblings do you have?” will not help sparking the romance between the two people, but will rather turn the whole interaction into a stale, stiff, interview-like conversation instead of playful flirting that it should be.

Some of the other questions that are although innocent, still contribute nothing useful or attractive to a first-date conversation are: "So, tell me about yourself" or "What do you like to do for fun?" - we have all asked and answered those questions so many times so why even bother to take our conversation with a person we hope to attract and create romance with into that boring, "stiff" direction?

Surely there is nothing inherently wrong with those open-ended questions about where a woman lives, what she does, how many siblings she has, where she went to school, what her sign is, what her favorite color is, etc., but these questions contribute nothing to your coming across as an interesting and attractive guy. On the contrary - they convey a bad message - that you really have nothing interesting to say or ask and that you are just like anybody else - you are trying to fill the time and avoid the awkwardness of having nothing to talk about. This must mean that you are uncomfortable in such social situations and that you are unable to have a normal conversation where people simple talk about things instead of using convesational "crutches."

Avoid asking those boring, typical question early on and especially on a first date when you are out with a woman. You will have plenty of time to ask your date all of those questions later if you get along and continue seeing each other. Instead, skip all those pleasantries and introductions and dive right into the interesting stuff as if you were talking to a long-time friend. Share your opinions and views on life, environment, people around you, celebrities, movies, and your traveling experiences. Make fun of celebrities or something or someone that you observe at that very moment. Be sarcastic but not negative, make fun of things, make fun of yourself and tease your date playfully to make your first date exciting and memorable to both of you. This is one of the most powerful ways for you to convey your personality to your date and come across as a fascinating, attractive person whose character stands out conspicuously from the rest of the guys out there.

Remember, there is nothing worse than coming across as a boring guy to a woman, and the best way to not be boring is sharing your opinions on a variety of subjects and inviting her to do the same. Surely you are risking to have a disagreement on any given subject with a woman, but don't worry about it. It's a good thing to disagree with another person on something as long as you know how to do it in a civilized manner and not turn it into a fight. For instance, if a girl says "I hate Britney Spears... she is so crazy and can't even take care of her life with all the money..." you could say - "You know, I wonder what she is really like - as a person. I mean, all the information we have about her is based on what we hear in the media. She might just be a very different person in real life..."