65 Men Reveal The Moments Their Girlfriend Went From Future Wife To Absolutely Not

Asking, “How long should a man take to propose?” is like asking, “How long is a piece of string?” It really depends on the couple and their relationship. 

When The Knot surveyed nearly 8,000 recently engaged couples in 2024, 30% had dated for two years or less before taking the next big step. 53% were together for two to five years, and 17% had been in a long-term relationship of six years or more. 

There’s no one-size-fits-all, say many experts, including Amy Nobile, a dating coach and bestselling co-author of Just When You're Comfortable in Your Own Skin, It Starts to Sag.

"I want people to know that they have to ask the tough questions upfront in a relationship before they know if it's right to be engaged to somebody," she told The Knot. Nobile references what she calls the "three-four rule." It suggests people ask four important questions by the third date, or within the first three months of the relationship. 

The first is, “Is there chemistry or a connection?”

The expert says while this might seem obvious, sometimes when people ponder this question, they realize that the connection isn't as strong as they’d like it to be, or that the chemistry isn't quite there.

The second question, according to Nobile, is, "Are you aligned on core values?"

"Whether it's love, humor, family, honesty, integrity or kindness, journal your values. I always say a journal is your best friend," explains the expert.

Award-winning licensed clinical psychologist and the founder and CEO of Madison Park Psychological Services, Yasmine Saad says couples should be aligned on several core values, like children, religion, trust, communication, respect, and boundaries.

The experts agree that being aligned on core values will ensure that they remain bonded despite other differences.

“It also ensures that each party can be fulfilled, as living by one’s values is one of the key components to a purposeful and happy life,” adds Saad.

Now onto the third question to ask yourself long before getting engaged: "Is your partner emotionally mature and available?"

"That means you should ask about their past relationships, their part in the breakup, how they healed from it and what they want to do differently in their current relationship," explains Nobile.

Saad adds that if you’re going to spend the rest of your life with someone, you need to be comfortable with them. This concept applies to every aspect of your relationship, she told Brides.com. You should feel safe to be your authentic self and voice your opinions, and vice versa.

"Is your partner ready, in the same way that you're ready, to take the relationship to the next level?" is the final question Nobile suggests you ask yourself.

"We have to talk about these things," says the expert. "Some people will say to me, 'Oh, no, that's too scary. What if asking that question freaks that person out?' And my answer is, 'Well, there's your answer.'"

Saad agrees. She says while there are certain aspects of a proposal that should, or can, be kept secret, the two of you should both be on the same page when it comes to whether or not the time is right.

Saad believes that the two of you should have already discussed the possibility of marriage before the proposal happens.

"Simply put, if you and your significant other are really ready to move forward in your relationship, you should have already had a conversation about tying the knot, where you express your mutual desire to host a wedding in the future and commit to one another for a lifetime," explains Brides.com.

Many relationship experts say it's best not to rush into things, and that you should date for at least one year before taking the plunge. This is generally after the honeymoon phase has passed, and you're no longer looking at your partner through rose-tinted glasses.

"Those who get engaged after three or more years are 39% less likely to get divorced than those who date for just one year," reports Brides.com, adding that on average, couples date for about 2.5 years before committing to one another for a lifetime.