Entering a Conversation with Others

As fun as it can be to go out by yourself in San Francisco, not many people venture off on their own.  Sometimes you find yourself stuck in a situation where you want to talk to someone you find attractive or interesting but they’re in a group or with a friend.  One of the toughest situations is starting a conversation with someone who’s brought a friend because it’s intimidating and sometimes the person puts off a less social vibe.  The first and most important thing to establish is if the person is looking to talk to someone or if they’re just out to have a good time and catch up with their friend.

I’m going to review some scenarios that show how you can start a conversation and analyze what the person’s motives are.  There are a few steps and observations that I’m going to go over that can make all the difference!

Deciding if they’re there to meet someone can depend on where you are.  The circumstances change depending on the venue and environment.  Your approach will be different for people that are at a loud venue or club opposed to being at a quiet lounge or even a coffee shop.  The approach will also vary depending on if you’re male or female.  Females typically don’t have to do much more than a few basic flirting techniques to get a guy to start a conversation.

Check out our article on Flirting Tips and Advice.

Men on the other hand have a little more work to do.  They need to be able to figure out if the women are there for “girls night” or if they want some company.  The biggest tell is the eyes.  If a women is looking around or not fully involved in the conversation with their friend it typically means they’re open to meet someone new.  If you can make eye contact once or even twice with that person, you’ve already kicked off the introductions.

When approaching a group or friends it’s important to not disrespect anyone. Avoid interrupting conversation or trying to sit down immediately.  It’s good to start with a hello and introduction.  If you're creative you can throw in a line about something relevant.  But don't try to hard to be funny and definitely don't say anything that someone could find offensive.  It’s almost impossible to remember everyone’s name but make sure you focus on remembering the person of interest’s name! 

If the conversation dies out or you begin to feel a little uncomfortable you can politely excuse yourself with a "well it was nice meeting you, I'm going to go [do something]."  If the conversation kicks off and you've been accepted into the group it's important to give everyone an appropriate amount of attention (let them all talk and listen to them) but give the person your interested in the most attention and even possibly try to make some more eye contact.  When you're talking to the whole group try to keep topics open and unpersonal.  If things are moving well and you're sitting/standing next to the person of interest and you've made some eye contact when talking, you can begin a smaller and more personal conversation with that person and eventually break away from the group for another round of drinks. 

If there is only one other friend then you need to be very respectful and polite to them. They're typically the one who will dictate if you stay and chat or not!  In this scenario you probably won't be able to break away from the friend, but you can entertain them with good conversation and plan another date or exchange contact information after the end of the night.

I hope this information helps!  The last thing to remember is confidence,  you have to be confident but appropriate to get accepted to the group and it's always good to try and make people laugh.

Keep an eye out for upcoming workshops for flirting and moving a conversation along on our Meetup page!



Arthur G. Bahr
Social Instigator for...


Do what you love... and love will find you