Many people will advise that men ask women questions about themselves, and to let them do the talking. While it’s true that women love to be heard and discuss their interests, they will equally be interested in what you have to say. For those who are shy, this may be fairly difficult. So ask her questions, but be prepared to give your responses and keep the conversations going.
1. The Best Questions
There is a lot of what not to ask a lady on a first date, but this list can go on and on. It’s best to have some questions prepared so you don’t get nervous and stutter around the point. Below are some idea topics to begin with.
2. Ask About Her Work
This is great because she either loves it or hates it, which means you’ll get to find what she’s passionate about or what she seriously dislikes. One question that works really well as a follow-up is a discreetly masked, “why?” If she responds, “I work at a hospital for children” respond by asking her how she got into it. Always remember, “why” can sometimes seem interrogating, so always ask it in a curious and positive tone.
Keep this conversation going by continuing to ask for details without ever prying into something that she seems disinterested in talking about. Ask questions such as: Do you enjoy the environment you work in? Do you plan to progress in this company, or is this a resume fluffer? Just remember, any questions you ask of her, she might also ask of you. So, be prepared with a few work stories, maybe even something that will make her laugh.
3. Ask About Specific Hobbies, Music or Movies
Questions that can drive a conversation right down a ditch are: What’s your favorite hobby/movie/band? Usually the questions, “What kind of music do you like?” is followed by a quick, “Oh, I listen to everything.” It’s much better to ask someone about specific interests. Ask her if she likes Pop, Metal or Alternative. Ask if she’s ever seen a movie that you enjoy, and then discuss your favorite parts of the movie, which can expand into characters, actors or directors.
When you want to know what she does for fun, think of activities you like and ask her if she’s interested in those types of things. People can’t respond very well on the spot, so asking something general, like what she does for fun, might draw a blank stare or a similar general response. If you ask if she likes tennis, you can find out if sports interest her or not. Asking if she likes museums, art shows or other exhibits will show you what kind of intellectual pursuits interest her. This is also a great way to invite her on a second date that highlights something you both would enjoy.
4. Ask About Siblings
This question is great if she’s got family. If she doesn’t, change siblings to childhood friends. Follow up with some silly story requests, and be prepared to share your own. Ask her if her siblings or friends ever played pranks on her that were really hilarious. Ask what kind of games she played as a kid, such as Nerfball tournaments or a Ouija Board night. Keep it story-related, and avoid asking where these people live now or what happened to them.
For this conversation, have your own stories prepared to tell. Avoid anything that shows what pranks you pulled. This can actually be crucial because the things you did in high school may not reflect who you are now, but they can make some feel suspicious of what you’re capable of. Get some of you best dad-joke stories or times when your mother was extremely angry, and share these stories as well.
5. The Awkward Silence
Awkward silence is appropriately named because it always follows an awkward statement. Some inappropriate joke, story or a strange response to something she said may make her retreat away from the conversation. Avoid these moments by never discussing anything too personal, too political or too passionate. These sorts of topics can leave people worried about the direction of the conversation, so they hush up and leave it be.
If an awkward silence does rear its head into your conversation, compliment her. It sounds a bit cliche, but if it’s genuine, she’ll still appreciate it. Try and think of something non-physically related when complimenting yourself out of an awkward silence. Tell her you appreciate her worldliness, her quick-witted comments or her intellectual responses. Complimenting her looks during an awkward silence will bring on an awkward request for the check.
6. Demonstrate Your Shyness
If you’re shy, run with it. While telling your stories, mention that you’re occasionally shy and don’t enjoy confrontation. Different women are attracted to different kinds of men, and when they know you’re usually fairly shy, it’s a compliment to their level of attraction because they managed to get you to talk with them. Leading with questions that you’ve got your own prepared answers to will break the silence long enough to make you both comfortable during the date.