My boyfriend is the first person in my circle of friends that I’ve ever dated. I knew he was interested in me for a couple of years, but the stakes felt too high. Somewhere deep down, I was afraid my feelings would evaporate after initiating something romantic, and things would get weird among my friends.

Finally, after a going-away party in the summer where he wowed me with his kindness and sense of humor, I decided my interest had sustained long enough. I drove from Ann Arbor, Mich., to Chicago for his 30th birthday with the intention of making my feelings known. After about a year of dating long-distance, we’re now living together and I’m vastly more committed than I have ever been.

The potential bliss in converting a friend to a romantic partner is everywhere: There are many happily-ever-after examples in pop culture, from “When Harry Met Sally” to “Friends” to “How I Met Your Mother” to “Always Be My Maybe.” Even Facebook is trying to play Cupid within your friend group: The social network’s new dating platform has a Secret Crush feature where users can find out if unspoken interest might be mutual. But there’s also potential for an awkward ending, where you’re forced to encounter your ex at every mutual friend gathering for the rest of time — and your pals may also be privy to how you treated them, who ended it and why.

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In many ways, developing a friendship is similar to that early dating stage before you’re officially “in a relationship.” You might not be going on dates, but you’re learning about one another in a casual setting. You’re gauging whether there’s an easy rapport, and if you want to spend more time together. You’re developing a foundation of respect and understanding for this person’s character. This is why dating a friend can be effective in the long-term, with the right communication.

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?

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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.”

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I could tell I was authentically interested in my now-boyfriend, because I realized how much I valued what he brought to the table. I learned he was constantly friend-zoned by other women, and I was genuinely surprised. I’d always found him attractive, physically and in terms of his personality. I could easily name five partner qualities that he had, like the ability to make me laugh and goals he was actively working toward. For me, it also helped that we had a natural barrier — distance — that allowed me to take my time. Eventually, when the idea of that distance didn’t deter me from dating, I knew I really liked him.

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. I can honestly say that my boyfriend is the only romantic prospect I’ve never actually dated; we were just instantly together. Which brings us to another important question ...

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What kind of relationship are you looking for?

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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. Caitlin Fisher, a 31-year-old woman in Cleveland, had just ended things with her husband two months prior to visiting her friend-turned-flame in Boston. “I knew that there was mutual attraction, because we had always been a bit flirtatious with each other,” Fisher says. On that trip, Fisher and her friend hooked up for the first time, and, after a few weeks, decided to date. They would alternate who visited whom, but her ex-girlfriend had “insecurity” and “jealousy” issues, Fisher says, which were exacerbated by the distance. Looking back, Fisher says she regrets becoming “girlfriend official” without first setting expectations. Fisher was not yet ready for a serious relationship and wanted to keep things casual. “My friend wanted to grow old together and have a happily-ever-after in a lifetime relationship,” she says. “Fresh out of a bad marriage, I was not in any place to manage that discrepancy.”

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.

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Fisher tried to stay friends with her ex after realizing it wouldn’t work romantically, but it was too late to go back without bitterness. “Trying to talk it out after the fact hurt her, and left me feeling frustrated,” she says. “Had we talked before we hooked up and decided to date, I think we could have salvaged the friendship if not the dating relationship.”

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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.”

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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, 30, from San Francisco, met Nick the first week of their freshman year of college. 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. “Our senses of humor 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.”

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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.

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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 datelike spot. See if you can go deeper and create “a vibe.”

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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.

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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 minimize 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.”

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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.

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