Before you try to convert your crush into a significant other, here are some questions to ask yourself – and your friend.

Are you really interested – or is this prospect enticing just because it’s convenient?

It’s important to determine whether you’re genuinely interested in your friend, says Lindsey Metselaar, dating expert and host of the millennial dating podcast We Met at Acme.

“You should make sure this person is someone that you would want to date regardless of your friendship,” she says. “You should be positive that they have the qualities you would look for in a partner, and that you aren’t considering them just because of the history between you.”

If you genuinely value what a friend brings to the table, and can name, without effort a bunch of partner qualities they have – plus, of course, you’re attracted to them, not just physically, but in terms of personality, you could well be authentically interested. If you’re not feeling you have to rush to make a decision – because you’re friends, anyway, nothing’s changing there – you can work out if you really like them “like that”.

Once you press play, “things tend to move faster because you are already past the initial stages of getting to know each other,” Metselaar says. Which brings us to the next important question ...

What kind of relationship are you looking for?

Since you already know your friend pretty well, a romance could escalate quickly, so it’s important to be open about whether you’re looking for something casual or potentially long-term. If you’re looking to be together forever, and you’re not ready for a serious relationship, you need to be upfront.

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If you’re not ready for something serious, it might be best not to date a friend. Ghosting, lack of communication, and being wishy-washy hurts when it’s someone you’ve only been on a few dates with; it’s worse when it’s someone you’re already close to.

“If you’re selecting a partner because you know they’ll jump at the chance at dating you, and you know in your heart that it’s temporary or seasonal, I recommend that you stay in the friend zone for the benefit of the friendship,” says Julie Spira, a dating coach and online dating expert.

If you date a friend and then break up, it can be hard to go back to friendship without bitterness. At least if you lay out expectations beforehand, there’s more of a chance the friendship can be salvaged if the s**t hits the proverbial

The friend I have feelings for is in a relationship. Do I say something or wait for them to break up?

In most cases, if you want to date a friend who is not single, it’s best to let that friend end their current relationship without any interference from you, Spira says.

“Things will get complicated if you are responsible for potentially breaking up your friend and their partner,” she says. “Your confessional talk could result in a relationship overlap, and there’s no chance of a good ending for all.”

It’s best, Spira insists, to let nature run its course.

But sometimes it’s extremely obvious there’s a rare chemistry between you two. McCall Renold, from San Francisco, met Nick in the first week of their first year at university. They hit it off quickly, but Nick had a long-distance girlfriend. As their friendship deepened, it became clear to everyone around them that they had something special.

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“Our senses of humour matched, and we just seemed to ‘get’ each other,” Renold says. “It was definitely strange how close we became without becoming romantically involved, evolving into a friendship that was so close we were basically dating in all but the physical ways.”

For three years, as Nick’s long-distance relationship languished – and their friends and family thought they should be dating – Renold finally cracked. “I said, ‘What are we doing here?’ ” she recalls. “’We both clearly have feelings for each other, and everyone sees it!’”

Nick broke up with his girlfriend, and they started dating immediately, but they kept it quiet on social media for a while out of respect for his ex.

We’re both single. What’s the best way to broach the prospect of dating?

If you want to date a single friend, it is best to keep it light. “Treat them like a friend, and start by getting to know each other; then go for drinks, and see what happens,” Metselaar says. Extend an invite, but don’t invite others. Pick a date-like spot. See if you can go deeper and create “a vibe”.

If you’d rather take a direct approach, Spira suggests wading into the conversation as theoretical, perhaps: “What would you think about us as a couple?” Or: “Have you ever thought about us dating?” If the answer is no or there’s an awkward pause, you can probably back away fairly quickly by laughing it off.

Metselaar says if it’s a “go”, talk about whether you’re going to be open about your newfound status with any mutual friends.

If your friend doesn’t want to date, how do you minimise the awkwardness?

This is obviously the most painful outcome, which is why it’s important to prepare for rejection and awkwardness as real risks before you express interest in dating.

Wendy Walsh, host of the iHeartRadio podcast, Mating Matters, is all about making “a bold move” to see what happens. You’ve likely noted the qualities you like, know a lot of the bad (so there are few surprise negatives), and have observed how they treated past partners.

“You’ve already created the glue for long-term monogamy, which is an emotional connection,” she says. “But just know if your attraction isn’t mutual, you’ll likely lose the friendship,” she says. “So think long and hard about how valuable your platonic friendship is before you make that move.”

How to get over a crush who doesn’t reciprocate your feelings

If you’re shut down, be clear that you would like to remain on good terms. “If, after opening a dialogue about dating, the feelings are mutual, let your friend know how much you cherish your friendship,” Spira says.

And then, be a good friend. Do not press the issue. One declaration and a clear conclusion should be the last time you discuss it.