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 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. 

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Why you should consider a group date over one-on-one


  • Group dates are natural icebreakers. Right off the bat, the edge is taken off and “people don’t feel as awkward because it doesn’t put the pressure on two of you to keep the conversation going,” Sullivan says. “It can help make the whole process smoother.” If you’re a bit shy or get so nervous you can’t relax and be yourself during a traditional one-on-one setting, this is perfect for you.
  • Guess what? If you don’t jive with one of the women, you aren’t committed to spending the whole day or night with her. You have other people there. 
  • “It’s good to go on a group date because then you can see how the person interacts in a group setting: How she gets along with others, if she’s friendly, if she can hold a conversation, and how she holds herself in general,” Sullivan says. It also exposes the not-so-great qualities pretty fast. Is she awkward? Does she need the spotlight and attention on her at all times? Is she high-maintenance or a narcissist? Is she insecure? 
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  • If you or someone else has a super dominant personality, it can take over and start leading and dominating conversations, which can be super-annoying,” Sullivan says. This is great practice for a one-on-one date, too: Learn to sit back and listen every once in a while. We’re not saying you can’t be yourself, but don’t make it so people feel like they can’t get a word in edge-wise. 
  • You may have some competition—especially if two people like the same guy or girl,” Sullivan says. That’s only natural. But, in most cases, adults can act like adults. So long as you and your buddies lay down some ground rules ahead of time. 

Sullivan adds:

“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.” 

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How to go on a group date

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.

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