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Engagement season is coming up, and we all know that one couple we’re really rooting for. They’ve been together for practically a decade, they act as a unit, and maybe they even own a dog together—but there is no sign of a ring yet. Naturally, you’re curious to know if this will finally be the year.

Maybe you’re married and just enthusiastic to have more married comrades, or maybe you’re single and just excited for another round of parties. But nonchalantly probing about when it’s going to happen can poke at scars or bring issues to the surface that your friend might not want to address in casual conversation.

I spoke with several women who either had a very long courtship before engagement or are still dating in years-long relationships. Here are some things they wished more people knew about their situation.

Before you begin, ask yourself: ‘Are we even that close of friends?’

One thing all the women told me was that the offense was often mostly caused by who was asking rather than what was being asked. So, before you get down to brass tacks, consider if you know this person well enough to make this personal inquiry. If you’re curious but aren’t sure if you are close enough to her, consider this: Has she ever confided in you before? Would you feel comfortable discussing your relationships with her?

Even if your answer is yes, and you’re speaking with your BFF, choose your words tactfully. If you’re close friends, it’s normal to talk about whether marriage is in the future, but make sure you don’t say these things:

‘When’s the wedding?’

In this case, it does not pay to be direct, playful or not. This approach will probably come off as prying at best, a full affront at worst. There is likely a lot more going on in your friend’s life than a looming engagement, so ask about the things that are currently on their plate before going into the (hypothetical) wedding talk. If you're close, your friend will most likely bring up her relationship on her own at some point.

‘Will there be a wedding this year?’

Similar to the above statement, but with a twist. When you ask about a specific timeline, it can get awkward, as it puts a weird pressure on the person you’re asking, especially if there isn’t an engagement nearing. After all, they may feel as though they need to defend themselves, as the follow-up question is inevitably, “Why not?” So take a step back, and give her a chance to talk about the bigger picture, instead of making her feel as if something is wrong.

Say instead: “Have you guys talked about getting married?”

‘What’s the holdup?’

Maybe it’s a given that this couple will get married, but there are a million reasons that the time may not be right to get engaged. Maybe there are family issues at stake, maybe they are overwhelmed with school or work, maybe they're in the middle of saving up for a wedding or ring—the list goes on. Any of these things could be uncomfortable for someone to talk about at point-blank. Avoid an awkward silence by keeping pointed questions to a minimum.

Say instead: “Are you and your man in a happy place right now?” or “What do you and your boyfriend have going on during the holidays?”

‘So, are you focusing on your career?’

"You would be shocked how often people ask this!" one woman I interviewed lamented. The assumption that a successful career is the reason to hold off on an engagement is an outdated one. There is no reason that a woman can’t be engaged and continue to work at optimum level. Maintaining a relationship while working full-time has arguably never been easier. Besides, would you ever ask a man if he was able to balance an engagement and a thriving career?

‘I don’t blame you for being antsy! He’s taking forever!’

Maybe your friend is dying to get engaged. How do you handle her frustrations without trash-talking her boyfriend, ultimately making her feel worse? In this scenario, a couple of sensitive questions and two good ears for listening are your best bet. Ask her how she’s feeling, and be there to hear her out. If she does ask for your advice, it’s usually safe to encourage her to gently bring it up with her S.O. You won’t be able to solve it—just let her know that you're there for her no matter the outcome.

Say instead: “Let’s figure out how you can bring it up even though you’re nervous.”

‘But wait, are you just not ready?’

Read the room! Take a hint! If your friend replies by using short or vague answers, don’t press the issue. She doesn't owe you an explanation for her relationship and will potentially open up about it when she's ready, as long as you don't pressure her.

Say instead: “If you want to talk about it, I’m happy to listen when you’re ready.”

Sure, it’s natural to be curious, but when it comes to friends, you should always be listening instead of prying. It’s your role to be patient with her during the waiting period, as you’re sure to be one of the first people she calls when the question is popped!