Valentine’s Day is coming up and a lot of guys are maybe contemplating asking their lady to marry them. Here’s a quick guide on how not to mess it up. 

Know the Answer – We’ve all seen the YouTube videos of the marriage proposal fails, so know what she’s going to say. Before you pop the question, you should have already had some discussions about getting married. If you haven’t had those discussions already, you may want to bring up some of these topics: income sharing, starting a family and where you’ll live, but don’t preface these discussions by saying, “We need to talk.” We hate that. Instead, when you see kids at a store or running around the neighborhood, casually bring it up like, “You ever think about having kids?” If she says yes, then ask, “Have you ever thought about having kids…with…me?” Or if you’re at a wedding, ask her if she has ever thought about what her wedding would be like. If she readily gives you answers, that’s a good sign. If she gets uncomfortable and clams up, then you know she isn’t ready.

Be You – If you try and do a super duper over the top proposal and it’s just not “you”, then she may expect you to be super duper over the top all the time every day.

Buy a Ring You Can Afford – You may want to give her a huge sparkler, but if it’s way more than you can afford, don’t do it. It’s better to get a smaller diamond now and start off your life on the right financial foot, rather than begin your life together in hock to your eyeballs. Give it a few years and after you’re making more money, take the smaller diamond, split it into earrings, or reset it in a pendant and get a bigger diamond ring.

Ask Her Dad First – Regardless of how intimidating he may be, you need to ask him, especially if your girlfriend has a close relationship with her father. You’ll score major brownie points with him and likely your future Mother-in-Law. The only exception to this rule is if she has absolutely no relationship whatsoever with her Dad, then you can skip it, but you may want to check with her mother.

When in Doubt – Go with the small, classy and private. If you know she’s easily embarrassed, don’t go anyplace where you’re going to have an audience. Instead, rent a limo to take her to a nice dinner (maybe the place you went on your first date) then take a walk hand in hand through your favorite city park and pop the question there. Have a bottle of champagne in the cooler of the limo to celebrate the occasion. Or, call her bestie and her sister and tell them what you’re up to and have a few bottles of champagne on hand and after you pop the question in the park, drive around and grab them so they can be a part of the celebration.

These are all very romantic gestures that show you care about her feelings and the people in her life which may just make her a little more likely to say yes.

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