When Should You Propose – A Guest Post by Ricky Anderson

Ricky Anderson is a guy.  he writes stuff.  this is is the second time he’s written stuff for my blog.  he’s cool or whatever.

I remember it like it was yesterday.

Jana and I had been dating for a few months, and things were starting to get serious. We had even traded a few “I love you”s. One of my high school friends was getting married, and we were invited to her wedding. It was an outdoor wedding; a fancy get-up at the golf course. During the ceremony, Jana leaned over and whispered to me, “Sarah sure has on a pretty dress.” That’s what she said, but what I heard was, “I hope my dress at our wedding, which I have all planned out in infinite detail, and shall commence in the next six minutes, is that pretty.”

I went from Joe Cool to Chicken Little in half a second flat. I literally broke out in a cold sweat and wanted to take off running down the fairway. This, ye single gents, is how you tell you are NOT ready to propose. Obviously the story doesn’t end there, because then I wouldn’t be married and I wouldn’t be qualified to tell you when you’re ready to propose. Well, I am married, and I am qualified to tell you how to plan your love life.

What makes me qualified, you ask? It’s simple: I’m writing this post and you’re not. So quit interrupting and look at my hastily organized list:

You Are Ready to Propose If All the Following Items Are True:

You’ve met a girl.

She’s available.

You’ve been dating each other longer than a Bachelor contestant.

You respect each other’s views on the big things in life like religion, money, politics and how far away to live from your possible in-laws.

You don’t have fights; you have disagreements…and you resolve them.

You can be yourself around her.

She doesn’t run from your B.O.

You don’t run from her cooking.

You love her.

But the biggest factor for me was when I got to the point that the idea of not being married to Jana scared me more than the idea of being married at all. I couldn’t imagine myself without her. I would glance at her hand and get actively bothered at her bare ring finger. I wanted other guys to know she was taken, and they could buzz off. I saved and saved for her engagement ring. When I got a smaller paycheck than I planned, thus moving the big date farther into the future, my best friend spent an hour calming me down.

When you think about your future, and she is all you want, that is how you know you’re ready to propose. Good luck!

okay peeps.  proposal stories.  let’s hear’em. 

feel free to post a link to one of those youtube videos of crazy proposals if you don’t have one of your own.


14 comments on “When Should You Propose – A Guest Post by Ricky Anderson

  1. Guy: Will you marry me?
    Girl: Only if you brought me a small cup of coffee!
    Guy: I came prepared.
    Girl: Oooohhh! Yes, yes I will marry you!

  2. JBen says:

    My fiance and I ran the St. Louis half marathon together in april. I had the ring in a pouch on my belt. About 2 miles from the finish line I was done. I didn’t think I could keep going. But she looked me in the eye and said “I love you. And we are going to finish this race together. You can do this. Now let’s go!”

    If I wasn’t sure before that, I was all in at that point.

    About 10 yards from the finish line I grabbed her, dropped to my knee and asked her to marry me.

    She said yes.

    It was awesome. The Wedding is in november.

  3. Save for your engagement ring. Don’t spend your student loan refund on it.

  4. Tony Jacobs says:

    Short version: Poor college student, working full time. Wanted to marry my best friend. Sold the only thing i had of value, X-Men comic collection, to buy the best ring i could (it was the 80’s, but they were still collectable).

    Went to our favorite spot on the river, at night, full moon. i sang her a song i wrote. The last line… “will you share my life, will you be my wife?” (Cheezy) She didn’t get it. i sang the last lines again. She still didn’t get it… “Will you marry me?” i asked as i presented the ring. She freaked out, realizing she didn’t get it the first times. A resounding, “Yes!” was the reply.


  5. Mandie Marie says:

    My pastor slipped an engagement ring on his girlfriend’s finger during a really long prayer during a church service. They’re married now so I guess it worked, but I think she’s still a little peeved about it 25 years later.

    I feel like there should be a follow-up post: Now That You’ve Decided to Propose, Here’s How You Shouldn’t Do It.

    • sharideth says:

      my friend jason spent months playing with his girlfriend’s rings (she wore several). he would slide them on and off while they were watching tv.

      she got so use to it she didn’t notice until about an hour later that she was wearing an engagement ring.

      brilliant move.

      they’re divorced now, but whatever.

    • Oh man, we could have a lot of fun with that one.

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