Meet the experts: Sarah Jones is a relationship expert, and founder and CEO of coaching website Introverted Alpha, and Sameera Sullivan is the CEO of Lasting Connections, an elite matchmaking service. "This is a great ice-breaker because it's a little mischievous and flirtatious," Jones says.
"It's a sign you'd like to know her beyond surface level, while still giving her the freedom to reveal what she wants to share—and doesn't." This question lets you get a sense of what she feels strongly about and whether she's spirited and heartfelt.
Key goals of a first date are to (a) see if you have a connection, and (b) find out if you and your date have any major areas of incompatibility. Why: Does the person have strong feelings or are they more easygoing and with milder feelings.
You also want to find out a little about your would-be mate's history and current interests.
If there's one thing that can ruin a first date and ensure a woman's first impression of you is a bad one, it's crappy conversation.
You need ice breakers, light-hearted queries, questions that provoke banter, laughter, and thought, as well as questions that dig a bit deeper and go beyond the superficial. If she hates planes, road trips, or has no desire to leave her hometown ever, that's a good indicator of her ambitions and desires (or lackthereof).
Is this just something that has to be there and happen naturally?
Or can I push it along by bringing up certain topics?