Here’s How To Start A Conversation With Your Crush

Can’t Think Of What to Say?

woman texting text with latte on the street

It’s nine o’ clock at night, and you’re thinking of That Person again. Sure, you may not have hung out since high school… but high school was a pretty great time, all things considered. You can’t even remember why you drifted apart in the first place. After the typical Facebook stalking and Instagram scrolling, the moment of truth has come: do you dare text them?

Whether it’s an estranged friend or a dear relative, it’s never a bad time to check in! Here’s eight different messages you can text at any time that are sure to make your person smile.

Just Checking In

If you’re thinking of someone, let them know! It’s never a bad thing to be on someone’s mind. (But if you hit that third “hey,” it might be time to stop texting and let them come to you.)

A Positive Message

Want to text someone, but don’t know what to talk about? Why not send a positive message! You don’t need a reason to be nice to someone, and random positivity can often be the best kind.

A Genuine Compliment

If you feel uncomfortable with sending off generic positivity, get specific. What do you love about the person you’re texting? Is it their nose? Their sense of humor? If you’d be excited to get that compliment in your inbox, they will certainly love to see it in theirs.


Specific encouragement can be some of the best kind, because it shows you’re present in your conversations with friends and support their goals. If you’re reminded of a project a friend is working on, check in to see how it’s going! They will be delighted to share their goals with someone who cares, and you’ll win points for caring in the first place.

Little Reminders

Whatever it is that made you want to text someone in the first place, let them know! It could be an old photo, a dress at the thrift store, a good book… the only thing better than being on someone’s mind, is having a friend who sees you in the small things. Be that friend!


There is never a bad time for memes, never. Don’t let anyone tell you different.

An Invitation

Inviting someone out (or in!) can be nerve racking, but it is always worth it. If you want to see more of that person, that’s the best way, and the absolute worst thing they can do is say no. Even then, you’ll have an answer… Which is much better than spending your whole life wondering if they would have said yes!

Something Sentimental

There’s nothing wrong with “I miss you.” If you feel it, you’re allowed to say it. You might reopen contact with someone you thought you lost, or take a trip down memory lane with an old pal. Either way, nostalgia can be a great feeling when it is shared.

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