Waiting and wondering when your guy is going to pop the question can be agonizing, especially if you are not the type to sit back and take life as it comes. For those who have been go-getter "Type A" achievers since birth, not having any control over “achieving” the state of holy matrimony is beyond frustrating.
There are lots of reasons why guys are reluctant to propose: he’s worried about money, he’s irreparably scarred by his parent’s nasty divorce, he’s not ready to give up his "freedom," etc. However, if your urge to merge has fallen on deaf ears, and you truly feel that the threat of losing you is the only thing that’s going to get him down on one knee, here’s how to go about it:
Timing. Although there is no rule about when you can start to discuss the possibility of forever-ever, try not to mention your preference for platinum vs. white gold engagement ring settings before the 3 month mark. And definitely never bring this topic up in front of friends, family or on national TV, Miss Jennifer Love-Hewitt. For best results, save the "pop-the question" conversation until you’ve celebrated every holiday in the entire calendar year.
Mood. Pick a time when you are alone with your guy, when he’s relaxed and feeling communicative ie., NOT when you’re both drunk, not during a 15-minute time-out of the final game of the NHL Stanley cup playoffs, and never during post-sex dozing. Begin by explaining that you have something on your mind, and be very direct about how your uncertain status as his future Mrs. is making you feel. Try to remain as calm as possible, turning on the waterworks will only make him edgy and uncomfortable.
Deadline. Whatever timeline you give him for proposing, make sure it is fair, and that you can be patient enough to hang out in limbo for that much longer. If you want a ½ carat and a 250-guest extravaganza before your next birthday, factor in things like his car payments, current status as unpaid intern, or the fact that he is still paying off students loans and adjust your expectations accordingly.
Outcome. Give your guy some time to marinate. During this stage, be prepared for both a proposal and a potential break-up. If he drags it out until the 11th hour, but turns up with that perfect princess cut sparkler, will the fact that he needed a significant nudge take any of the shine off the rock? And if he declines to be deadlined, are you prepared to accept his decision, pack your bags and start searching for someone willing to put a ring on it?
Your turn. Have you ever given an ultimatum, or would you advise a friend to give one? Why or why not?