Dating and Relationship Advice


Online dating is the new normal. So why is it still so hard to move past casual banter to meeting IRL? In 2021, that might mean a masked, outdoor meet-up or a virtual hang. But most would still prefer a socially distanced date to texting someone for days before it eventually fizzles out.

If chatting back and forth feels organic, here are some messages that can help take things to the next stage for you and your match.


“I’ve loved chatting with you on here. Do you want to grab a coffee sometime next week/this weekend?”

This gives them some time to prep for a date, and isn’t as spontaneous as asking them to hang out immediately. Coffee is low-stakes: not as awkward as breakfast and not as high-pressure as dinner. A FaceTime coffee in the comfort of your own home is also perfectly fine.

“I know the coolest little (insert venue here) that recently opened. Do you want to meet there at X o’clock on X day?”

Don’t be afraid to be confident and name a suggestion. Obsessed with the indie bubble tea shop that just opened up next door? Ask your date if they'd like to meet you there. This lets your date prepare for what the activity is, and earns you brownie points for knowing a cool spot. When one simply brings up food or coffee, without suggesting any place in particular, it can feel vague and unsexy.

“What are the chances— we have the same favorite food/restaurant! Shall we meet up for a takeout picnic?"

When you're first chatting with someone, you ask them questions to find out what their favorite things are, and see if there's something the two of you have in common. Ideally, they’ve already put this info in their bio so you can lead with this line, but you can also reach out to them and find out what your ultimate shared indulgence is.

“Pick one of these emojis, and that’s what we’ll go get/I’ll cook for you on our dinner date🍕 🍣 🌮 🥡 🍔 🍝"

Maybe the chemistry is 100% there and you feel ready for a dinner date! Whether it’s restaurant week or a home-cooked meal (which we wouldn’t suggest for the first date— maybe the second or third), this is a cute and flirty way to take the date offscreen into in-person territory. Emojis are always a win when used correctly and appropriately.

“I’m getting cabin fever sitting inside. Want to take a walk?”

This is a very real problem for people during Covid. Even when there’s not a pandemic, we all need to get out of the house or office and stretch our legs. It’s also a cheap and low-pressure way to get to know each other better. Points if one (or both) of you has a dog, which is another conversation starter and bonding point.

“If you could go anywhere in this city, where would it be?”

This is a unique and slightly unusual way to transition to the "let's meet up" conversation. Maybe it’s a place they haven’t visited since quarantine, or perhaps there’s a nature trail they’ve always wanted to walk but never had a chance to try out. It’s an easy way to both discover their interests and get a quick idea for a date.

Don’t message—call them on the phone!

We know, we know. This is a nightmare for a lot of millennials. But it’s a classic way to plan a date, and you get an answer right away. (Certainly better than playing tag via messages.) Seriously, just pick up the phone and ask them on a date. It’ll take less than five minutes, and you won’t end up stressing out for hours about what message to send. Plus, it’ll give you a chance to connect, hear their voice, and read their vibe.