Starting conversations–Tips to help start, maintain and end conversations gracefully

One of the most difficult things to do when meeting a new woman is starting a conversation. There are a few things you can keep in mind to make it a little easier though.

One thing to remember is to keep your internal monologue in check. If you find that you’re struggling with starting conversations, it may be that you’re telling yourself negative things internally.

Things like, “I’m going to bother her”, “She’s going to think I’m boring”, “I’m not interesting enough for her to talk to”, “She’s going to blow me off”. Do any of those sound familiar? I know they did for me before I worked on my conversation skills. Remember that negative self-talk is normal, but it isn’t productive. Just like anything else, practice and preparation really help to overcome the initial butterflies that you’ll experience when starting conversations with women.

Conversations are best started by asking questions or making observations. If making an observation, focus on something that you’re both experiencing or can both relate to. Making a comment about the guy with the foot-high Mohawk standing in line ahead of you, or the huge painting hanging on the wall in the waiting room offers a chance to break the ice without seeming awkward or canned.

If asking questions, the best bet is to use something that truly interests you as the inspiration. For instance, asking about the author of the book she’s holding on her lap on the train (and ACTUALLY being interested) is a great way to open up a great conversation. Just like when making comments, avoid using canned material if possible. “How ’bout this weather?” can be awkward. If you’re going to comment on something mundane, spice it up a little! “Can you believe how FREAKING cold it is right now? I thought it was going to warm up by now…didn’t you?” is a better bet.

Ok, so now that you’ve made first contact it’s time to think about the follow up that will help keep the conversation flowing. Starting conversations is half the battle, keeping them going is the other. This is where you can do a little home prep to have something ready to follow up with.

If you’re going to an event, think of something you can comment on when you get there, and a follow up like “so how did you hear about this?” or “what brought you here tonight?”. You can also keep up on current events that interest you, if nothing else just to be able to ask a woman’s opinion about them and to be able to respond intelligently.

While talking, make sure to weave your own experiences into the mix. This not only keeps the conversation going, but creates emotional connections that you can use to move forward or talk about again later. If you are asking how a woman found out about the little park you’re in, you may find out that she was looking for a place she could take her dog to without worrying about having to use a leash. Bingo! You may have a dog too, which is a great topic to expand upon. Or maybe your favorite niece loves dogs and coming here with you to play with them. From there it’s endless. “It’s Saturday, how are you lucky enough to have off during the day to come out here and enjoy it? (which leads to what she does for a living, etc)”, or “It’s Monday, how are you lucky enough to have off during the day to come out here and enjoy the sunshine? (see the pattern here, lol)”.

Another thing to remember is to let her talk. Sometimes we’re in such a rush to get all of our thoughts out that we don’t give the other person a second to interject. Remember that saying…something like, “we have two ears and one mouth, so we should do twice as much listening as talking”… you know the one I mean. Well, it’s true. Think about it. When someone actually listens to you it makes you feel good. You want to be the person that makes other people feel good!

A good way to make sure you’re giving her the opportunity to talk enough is to ask open-ended questions. Questions that start with who/what/why/how are good ones to use, like “what do you think?”, or “how about you?” They give an opportunity for her to expand on an answer instead of just using “yes” or “no” answers. And when she expands on an answer, it gives you more opportunities to pick up something else to talk about.

Even great conversations have to end–and you don’t necessarily want to go on for half an hour about common interests the first time you talk to her anyway–so ending a conversation gracefully is equally as important as starting a conversation. In the park example above you could end with, “I have to get going, but I really liked talking to you, maybe we could meet here later this week and I can meet this dog I’ve heard so much about”, or “I’m late for a meeting, but I’m going to be heading back here later this week to have lunch, should we meet up and enjoy some of the sunshine before winter takes it away?”.

As you can see, ending the conversation in the right way gives you a great, natural way to exchange numbers and keep in contact.

Finally, the best advice I can give you is to…PRACTICE, PRACTICE, PRACTICE. Just like anything else in life, starting conversations gets easier and easier the more you do it.

I’ve put together a package that will help you become more confident and outgoing that I think will really help if you’re struggling in those areas.

Talk soon–JT