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By and large, the most frequent complaint I hear from my single and dating friends is that it’s difficult to keep conversation going with guys you have just met or matched with on an app. Whether you don’t know what to say or you struggle to keep the conversation moving forward, there are little tricks you can apply that can vastly improve your conversations—and your odds of scoring a date.

You can take my advice literally, of course, but what will help you most is to keep a few basic principles in mind as you venture through the wide world of dating. First, think about any great conversation you’ve had. It’s the back and forth, the sharing, and the questions that keep it interesting. Second, don’t forget that everyone is human. At the end of the day, we all just want to meet someone nice who makes us laugh.

Here are four basic principles that will make sending the right messages, on your phone or IRL, a whole lot easier.


Say this: “[Three waving hand emojis] How’s it going, [insert name here]?”

Not . . . “Hey :)”

OK, so I’ve spoken about all the luck I’ve had with this line before. I think it’s cute and a bit more fun than your basic intro line. Also key? It’s a question. A complaint I’ve heard from a lot of my male friends who use apps such as Bumble (where women must message first) is that women basically insert a filler (such as a single emoji or the word “hey”) to start a dialog but leave it up to the guys to engage a real conversation.

Show your confident side in small ways by making an effort to get a real conversation going. Even if you’re new to this format of dating and you’re used to being “chased,” this is a pretty low-key, low-risk introduction.

The IRL equivalent: Out in the real world I suggest the exact same thing. I mean, sure, you could just go up to a guy and say “hey” and smile. But I dare you to ask him how his night is going, what coffee drink he ordered, or that classic pickup line, “You come here often?”


Say this: “I love your nineties heartthrob haircut.”

Not . . . “You’ve got great hair.”

The point here is that being specific and a little bit silly can get you a long way. Sure, genuine compliments are nice, but they can also make people feel a little squirrelly if they’re deployed too soon and based solely on physical traits. Rather than blatantly stroking this guy’s ego, I suggest using this line shared with me from a Bumble user at a party the other night. It’s a compliment, sure, but referencing the nineties and using the word “heartthrob” is more playful than praising. This intro line is flattering and also a bit of a thinker: Does she mean Zack Morris or Joey Lawrence? Try something like this, and you’re basically guaranteed a fun conversation from here on out.

The IRL equivalent: Introducing yourself this way in person is flat-out bold. Make no mistake though, I’m here for it. We hear all the time that men say they love when a woman makes the first move, so why not put that theory to the test? Just like in a digital format, using this line will tell you a lot about a guy pretty quickly. If he brushes it off, if he doesn’t get it? He’s not for you. The guy you’re looking for will laugh, say thanks, and then probably offer to buy you a drink.


Say this: “I had brunch at Dudley’s on the Lower East Side and then went for a walk in the East Village. Later I went out for drinks in Williamsburg with friends.”

Not . . . “I had brunch with my friend Karen and then went for a walk with my other friend from college and then had drinks with a bunch of girls from work.”

See the difference?

If there’s one “iconic” question-and-answer exchange from the app dating era, it would have to be “How was your weekend?” and its response. You simply can’t avoid it—but you can make it more interesting. After discussing this phenomenon with a friend, she noted that whom you’re with on the weekend is not interesting to a person you’ve never met. What is potentially interesting to them is where you went. The places you like to go and the neighborhoods you visit say more about potential compatibility. It might turn out that you love the same pizza place on MacDougal Street or have passed each other while running on the West Side Highway.

The IRL equivalent: I’ve already outed myself as The Girl Who Talks Too Much, so it shouldn’t surprise you that I tend to include too many irrelevant details when recounting my weekend to a potential date. You shouldn’t be trying too hard to censor yourself in conversation, but keep in the back of your mind that you’ll probably find more common ground in discussing the “where” and the “what” rather than the “who” of your weekend plans.


Say this: “Thursday works, how about 8 p.m.?”

Not . . . “OK, sounds good!”

One of the problems with the casualization of dating that has evolved from app use is the parallel problem of vague plans. We’ve all become scared to be vulnerable, and it’s even affecting our ability to make a firm commitment to a single date.

I recently connected with a guy through Tinder, and we had a great first date. He immediately inquired about setting up a second. We settled on a day the next week, and I was thrilled. I gave him the ol’ “Sounds good!” and nearly threw my phone in triumph. Flash forward to the day of said date, mid-afternoon, and I still had no idea what time we were meeting or where we were going.

From conversations with friends, I know this happens a lot—but there’s an easy fix. If your guy suggests something like, “How about Wednesday?” instead of replying with “Sure!” or the equivalent, nail down the details. Along with your confirmation of the date, suggest a time that works for you. This gives you some agency in the planning and time to schedule your day or pick out what to wear.

The IRL equivalent: The real-life version of this conversation should play out similarly. I would first like to give mad props to the guys who are confident and mature enough to have an in-person conversation about setting up the next date—that takes real gusto in 2017, and it’s flattering as all get-out. If you find yourself in the presence of such gallantry, respond in kind by letting him know exactly when you’re available, just as you would over text.

Photo Credit: Cynthia Chung