This can be a very tough question to answer because the timing is different for every couple. Some guys pop the question when they’ve only know the girl for a week while others wait years to ensure that the timing is just right. Generally speaking, there is a right time and a wrong time to ask, but how do you know when it’s the former instead of the latter? In truth, you may not ever know for sure, but if you follow a few simple guidelines, you’ll have a much better chance of securing a “yes” when you drop to one knee.
1. Get to know her. If you don’t know what her response will be, then there’s a good chance you shouldn’t be asking. Don’t bypass the most important part of the relationship in your haste to reach the finish line. You could be avoiding a lot of hurdles that you’re going to have to jump at some point down the line. Better to get to know each other now so you don’t end up in divorce court later.
2. Move in together. There’s no better litmus test to see if you’re ready to propose than actually living with the person you want to spend the rest of your life with. Long after the honeymoon phase fizzles, you’re going to have find a way to make it work. So if you are compatible as companions and partners rather than just lovers, there’s a good chance you can make a go of it.
3. Drop hints. Find ways to bring up the prospect of marriage in casual conversation as a way to gauge her interest. If she is firmly anti-marriage, then now may not be the time to offer a ring. She might have other obligations (school, for example) that are keeping her from committing right now, so let it drop for awhile, but keep the idea fresh in her mind so you know when she’s ready.
4. Look at engagement rings. Her willingness to peruse the his-and-hers section of the jewelry store is a good indicator that it’s time to seal the deal. If you have to take her in and she finds an excuse to head to tennis bracelets, then you should probably back off. If, on the other hand, she has to drag you to the engagement ring counter, maybe it’s time to start thinking about where your relationship is headed.
5. Make it special…for her. If you know exactly how she wants you to propose (because she told you), then you’ve pretty much got a green light. If you have no idea what she finds romantic, you either need a refresher course on women or you need to spend a little more time listening to your lady.