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Dating is complicated. Gone are the days of boys meets girl, boy takes girl out, boy dates girl. Now, you need to sift through apps and Web profiles, create a color-coded calendar to remember if you’re meeting Molly from Tinder or Jessica from Hinge out for drinks Thursday, and Kelsey from Bumble or Tiffany from Match.com for dinner Friday. It’s a lot to juggle. It’s also a lot of pressure. And, if your personality tends toward introverted, then dating is an absolute nightmare.
Sound about right? If you’re struggling to commit to a dating service, don’t want to download an app, and can’t seem to relax during one-on-one dates, group dating might be an amazing alternative. Consider it your primer to solo first dates. We spoke with Sameera Sullivan, CEO and founder of Lasting Connections, for everything you need to know—from the best places to go, and what to do if you and your buddy are crushing on the same girl.
“I had a client that I was working with for a while. He was super shy and not so great on one-on-one dates. But he was OK in group situations with friends. So, I decided to put him in a group situation where there were three women and three men. He was able to open up and treat it like friends going out for dinner. He was less tense and actually had a great time. He was also able to learn a little bit from the other guys, too—to see how they were interacting with the women. You can learn a lot in group situations if you want to, and, in this case, I made sure to include two guys who were savvy daters. My client got some real-life coaching while being on a date and he didn’t feel awkward.”
Who to invite
“One of the best ways to meet people is by telling your friends that you’re looking,” Sullivan says. Ask your girl friends (or even your sister if she’s fairly close in age) to play matchmaker. See if they can think of single women who would be a good fit for you or one of your friends and have her bring them along on a group date. Ask friends who are comfortable meeting new women but aren’t going to suck all the oxygen out of the room and make the experience all about them. When you have a group of people who are kind of familiar with each other, or maybe haven’t met but know a friend of a friend, you have a far better chance of making a connection. If all of this sounds overly complicated, you can also try a dating service like Grouper to streamline the process.
Where to go
“Try to go for interactive environments for a first group date,” Sullivan says. Games are great for creating playful and flirty banter (not trashtalk). “A pub can be fun if you can also play pool and have other activities, as well as a bowling alley where there’s good music and food.” Keep things light, playful, and conducive to conversation.
What to say
“Think, Why should she like me?” Sullivan suggests. “Ask her questions, show interest in her, and share something personal about yourself as well.” Being genuine and asking good questions (with depth and meaning that dig below the surface) are half the battle. Don’t just talk about your work, what you’ve achieved, and what you have; this isn’t a resume. Ask her about how she grew up, her family, where she’s traveled to, what’s her favorite thing to cook? Ask questions that clue you in to her personality and make her feel special. Here are 50 amazing questions to ask and five you should always avoid.