Definitely not after she finds your pocket pussy. The best time is when, after years of working up enough courage and gastrointestinal moxie, she finally feels safe enough to poop while you’re home. Or you notice her noticing you, all half-naked on the couch, eating dry cereal with a steak knife while jeering at the judges’ decision on “Top Chef,” and she joins in.
What I’m trying to say is you’ll kind of just know. There’s no real “right time.” There are a lot of “wrong” times, such as at a baseball game where every couple on earth has gotten engaged in front of thousands of corndog-inhaling strangers, or when she’s trying to tell you that you have to leave because this is Brian’s house now.
The best time is after you’ve spent a while thinking about what each of you want in life. The absolute best time is after you’ve learned that healthy relationships aren’t about possession or control; they’re about being vulnerable, intimate and supportive, and taking genuine pleasure in giving to the other person.
The absolute absolute best time is when thinking about spending a very long time with that person gives you stupid butterflies in your stomach and makes you feel sick. Whether that’s on Valentine’s Day, near some sunset or in the hobo cave where you first met; it doesn’t matter. The timing and location of it is much less important than the intent behind it. Sure you could stage some elaborate flash mob thing in Home Depot that awards you fleeting viral fame, but that means nothing if you and her haven’t discussed it, made sure you’re on the same page, and made sure you’re excited as fuck to be married people. I’d say talk to her about what she thinks about being married, what she thinks about being married to you, what she wants and needs in life and how you can do it together … and then hire the acapella troupe to surprise her on her way home from the dildo store.