This is How To Start A Conversation With Your Crush, According To Dating Experts

Whether you’re crushing hard on a dating app match or really miss seeing your office fling IRL, getting a convo going with someone you’re romantically interested in can make anyone break into a sweat.

And with the rise of online communication and online dating, there’s fewer opportunities to “accidentally” bump into your crush at, say, their fave coffee shop (that they go to every Tuesday at 9 a.m.). Instead, reaching out means texting, using social media, or gasp calling them. (That’s still a thing, yes??)

The online dating game is full of, well, games, and unspoken rules–don’t double text, don’t start a conversation if you started the last one, blah, blah, blah. TBH, it’s a lot to consider, and can make the art of actually conversing even more stressful.

Like, what the heck are you supposed to talk about? What’s too much information? What’s too little? And why didn’t anyone give me advice before messaging my crush on Hinge 10 billion times? Oops, that one’s for me. (Good news: We’re still dating.)

Guidelines would be nice, which is why Women’s Health tapped relationship therapist Lisa Marie Bobby, PhD, LMFT for some expert-approved advice. Before you start typing, she recommends assessing your crush’s feelings to see if there is potential for any sort of relationship:

“Someone has to move this forward, right? Invite them to do something with you that’s ‘date-ish’ and see what their response is.” Taking that leap of faith is the only way for a crush to evolve into something more.

If you’re still unsure where to start (totally okay if you’re not ready to take that plunge juuust yet!), here are some go-to conversation starters to spice up your summer love life.

Rest assured, they’re “all great strategies to open the door to a conversation that allows you opportunities to get to know the person you have a crush on more deeply,” says Bobby.

Some suggestions may seem silly, but she notes that “asking questions and making small talk is the first step of establishing a connection.” So get to it!


Step One: Vibe check.
“It’s important to be extremely thoughtful and cautious about announcing your feelings to someone you have a crush on,” Bobby advises. Instead, the first step is to see if they pass a “vibe check” and reciprocate your romantic interest. In that case, these are the perf convo starters.

Send them a pic of your dog.

“He’s been sleeping like this all day. :)”

Talking about pets makes everyone happy. As soon as you send a pic of your adorable pup, they’ll be sure to respond with “😍” and “when can I meet them?” It’s the perfect way to get your crush to open up about their life, their furry friends, and, if they have a dog of their own, even get the ball rolling on a playdate/actual date!

Research shows pets are playing more of a factor in dating life. After all, they aren’t just cuddly companions, they’re part of your family. Women are particularly discriminating when it comes to a potential partner’s association with a pet. Noted!

Send a meme or a funny video.

Chances are, if you have a phone, you have a favorite type of meme. Maybe you can’t get enough of the “yeah, sex is cool but have you tried pizza” memes, or perhaps you favor ones related to a specific TV show or celeb. No matter your meme speed, try sending one to your crush and see if they pass the vibe check by noting how they react.

If you’re not into memes, try online videos or TikToks. Whether it’s one of TikTok’s unbelievably cute grandparent videos or a funny one that just doesn’t make any sense, TikTok has become always appropriate to reference and share.

Talk astrology with them.
“So Co-star thinks we should hang out.”
If you know your crush is into astrology, bringing it up in a cute way can help them see your love is written in the stars. If you’re lucky enough to be friends with your crush on Co-Star or another astrology app, you can check how compatible you two are or even wait for the app to suggest a day when the planets are aligned for you two. Maybe you’ll be as compatible as Olivia Wilde and Harry Styles. (Hey, go ahead and dream, dreamer.)

Also download Jay Bahd – Wosono Ft. O’Kenneth x Kwaku DMC x Kelvin S

Got a crush who doesn’t give a flying F about Mercury going retrograde? Don’t fear—instead, talk about another shared interest that will spark great conversation.

Ask if they’ve seen your fave popular TV show.
“Okay, weird question, but have you seen Love Island?”

Even if they haven’t seen the show in question, they’re bound to have some strong opinions about, say, Love Island. They’ll either be chuffed to hear that you also watch it or confused about why you use so much UK slang. Or if you need to discuss your Mare of Easttown theories with someone, try asking your crush if they’ve seen the latest episode!

By starting a convo about any popular TV show, you’ll either end up discussing how much both of you are obsessed with it or convince them to watch an episode with you sometime. Big win either way.

Step Two: Build the connection.

So you’ve determined that they share your ~interest~ and are ready to press play on your own personal rom-com. The next step is to encourage opportunities for connection. If you’re looking forward to a date with your crush or want to make a date happen ASAP, try these:

DM them a foodie Insta post.
“We have to try this! 😋

Who doesn’t love drooling over great pics of food? Maybe your fave foodie shared a pic of the meal they just had at a new restaurant in town or that vegan blogger you love just released a mac ‘n’ cheese recipe that is supposed to blow your mind.

Either way, your crush is gonna want to have a meal with you—and that is the perfect segue to asking them on a date! Whether you replicate the meal at home or go out for dinner, “inviting them to spend time with you (if you feel it’s appropriate and that they are interested in doing so) is the quickest path to assess mutual interest and have the chance to get to know someone more deeply,” Bobby suggests.

Bring up a memory you have of them.
“Omg, I was just thinking about that time…”

If you’ve known your crush for a while, talking about the past will remind them of all the good times you’ve already spent together. Plus, letting them know they’re on your mind is hot, hot, hot.

FYI: Engaging with your crush’s memory is a way of tapping into transactive memory, which is the stored and encoded memory that two or more people share. Stronger transactive memory systems are associated with stronger friendships, per a 2016 study published in the Journal of Social and Personal Relationships. If it works that well for friendships, why not see if it benefits other ‘ships, too?

Catch up on plans they told you about.
“How did you trip go? I’ve been dying to hear about it.”

Maybe last time you talked they told you about taking a family weekend trip to Maine or planning a special dinner with friends. Let them know you remember their plans—and care about them!—by asking how they went.

Questions are the key to connection. “Research shows asking personal and thoughtful questions is the best way to get to know someone, so don’t be afraid to ask follow-up questions to get past the small talk and into a more personal conversation,” says Logan Ury, Hinge Director of Relationship Science. Plus, a 2017 study in the Journal of Personality and Social Psychology shows that asking questions, particularly follow-up ones, increases your likability.

Get flirty.
“I really wish you were here rn.”

It’s a Friday night. You’re feeling brave and thinking about texting your crush. Why don’t you go for it?! Send them a flirty message about how you’re thinking about them and want to spend some time together. Just be warned: This convo starter isn’t for the faint of heart. Make sure they’ve already expressed mutual interest so you don’t end up hiding under your covers all Saturday due to embarrassment.

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