The summer before my last year of college, I went on a few dates with a guy I met online, who I’ll call Jeremy, and we really hit it off. Then, he got back together with an ex, and I got into another relationship shortly after. Once that ended a year later, I made a bold move: I Facebook-messaged Jeremy to see what he’d been up to. Turned out he was single, too, and we were able to rekindle things. 

What I did was admittedly risky. Jeremy could’ve still been with his ex, or he may have just not been interested. But for me, it was worth it. Where’s the line, though, between a risk worth taking and one that’s intrusive? What’s the most respectful way to reopen a conversation with someone things didn’t work out with?

The answer depends on why things didn’t work out in the first place — but here’s how to get back in touch with someone in a few common situations.

1. If You Ended Up With Someone Else

If you want to get back in touch with someone you originally rejected for another prospect, you’ll need to help them understand that now, they’re the one you’re into. “Let them know a little bit about the context of why you ended things the first time so that they can understand why you felt you had to see how the other relationship panned out,” says relationship expert and mental health consultant Adina Mahalli, MSW. “Also explain to them that you think very highly of them, which is why you haven’t been able to get them out of your head and why you’re approaching them with this suggestion in the first place.”

Then, make sure to be very available to the person so it’s clear that you’re not going to pull away again. “If you show them they are your number-one priority, you have a much greater chance of them actually letting you back in,” says life coach Stacy Caprio

Nicole Amelia, a 22-year-old executive assistant in New Jersey, rekindled things with someone she’d left for someone else by first just sending him some kind words. “What I did was message him and say, ‘I see you are doing great things, and I am proud to see how far you’ve come,’” she says. “I just wanted to send a lighthearted message that let him know, ‘I am still here and I am still supporting you, even if we haven’t talked in a long time.’ This led to us talking again, and we made it work from there.”

2. If They Ended Up With Someone Else

If social media or mutual friends tell you someone is single again, reconnect in a way that reminds them why you dated in the first place. “Be somewhat vulnerable,” says sex and dating coach Carmel Jones. “Shoot them a text that reads something along the lines of, ‘I’ve been thinking about you lately. Want to go to that dinner spot we love for old time’s sake?’ Don’t bring up the fact that you heard they were single again. That will be implicit.” In cases like mine, where it’s unclear if the person is single, you may want to tread more carefully by simply shooting them a “hey, how’ve you been?” message and seeing if they take the bait. 

Once you successfully reconnect, you may want to have a conversation about what can help you feel secure so that you’re not anxious they’ll leave you again, says Jones.

3. If You Got Busy 

Before reaching out to someone you were previously too busy for, double-check with yourself that you have time for them now, then explain the situation to them. “Understand that they might be hesitant to try again, and you might have to really prove to them that you are now ready to commit,” says Mahalli. It may help to schedule something thoughtful to do together, says Jones.

4. If They Got Too Busy

Tread carefully with this one, because you want to make sure they’re now willing to make time for you. If it seems like their work or whatever made them busy in the first place has changed, you can test the waters with a text like, “Hey there! I came across this wine tasting I think you might like. It’s on Sunday at 1 p.m. Can you make it?” says Jones. “Keeping it casual yet also time-sensitive allows them to be able to visualize that time in their schedule without stressing them out or forcing them to come up with plans.” 

It’s very possible for two people’s once-disparate dating goals to eventually converge.

5. If You Didn’t Want The Same Thing 

It’s very possible for two people’s once-disparate dating goals to eventually converge. “As time passes, people and priorities change. And with this, compatibility changes too,” says Mahalli. “Send them a message or give them a call and explain your change of heart. Make it clear that you are now on the same page about the former deal breaker, and ask them if they’d be willing to try things again.”

You may need to apologize if your previous lack of interest hurt the other person. Jennifer B., a 35-year-old publicist in Brooklyn, New York, reunited with someone who previously didn’t want to get serious after he messaged her, “I know you must hate me right now. But I’d like to talk to you about everything that happened, if you’d allow it.”

6. If You Broke It Off For Personal Reasons

If something was going on in your life that made dating challenging, tell the other person what was happening. “Elaborate on your rationale for ending things before, explaining that you did not want to waste their time if you could not [give them what they wanted]” says Mahalli. “Say that you are now in a different place — one that allows you to give things a real chance.”

7. If They Broke It Off For Personal Reasons

You’ll want to treat a former fling’s personal issues with sensitivity. So, Jones suggests saying something like, “Hey there. I hope everything has gotten better with your situation. I was wondering if you were ready to take your mind off of it by meeting me for a dinner date.” This shows that you’re both respecting their space and ready to be there for them if they’re interested.

8. If It Ended Due To Distance

If you two didn’t previously live in the same place, but one of you has moved, you have a good opportunity to get back in touch. Start off casually by inviting them to coffee or a favorite hangout place in your area, says Mahalli. If a lot of time has passed, you could even offer to show them how things have changed since they left, says Jones. “Once you have a chance to hang out, sparks might fly, and you just might find yourself [dating] them,” says Mahalli.