Dear Crabby, How Do I Propose to My Girlfriend?

Dear Crabby,

I am ready to propose to my girlfriend, but I am really nervous. Can you give me some pointers or suggestions of how to go about this?

Sincerely, Ready Eddie

Dear Ready Eddie,

I remember well the days of preparation and planning that went into that event.  For me it was not so much the actual question and possible answer that was the cause of anxiety, but rather the consequences of failure that caused concern.  I know that many lovebirds will go on romantic dates filled with horse-drawn carriages, roses, and string quartets; however, that was not my style back then, or now.  For me, urgency took priority over romance on the day my CO (Commanding Officer) told me that I would be serving another year overseas unless my life circumstances prohibited it.  When I asked what circumstances might prohibit that, he replied, “Death, dismemberment, a jail sentence, or marriage.”  After pondering all my options and being fairly confident that the love of my life would say “yes,” I decided to take the plunge. I called up some fancy Italian place that I heard about for dinner and told the little woman to dress fancy for the evening.  I swung by a jewelery store on my way, figuring I could pick out a ring real fast.  Looking at all the beautiful rings and knowing how little I had stashed away, I simply asked, “Where’s the cheapest one you got?”  They showed me a ring that I thought was perfect.  I then went to my buddy’s to borrow his suit.  It was a little tight, but I like them unbuttoned anyway.  I swung over to the little woman’s to pick her up next.  I went ahead and asked if her pop was home so I could get that out of the way too. He was and I got right to the point with him. He was a little shocked; I assume it was because I was such a good catch for his little girl. We worked out a couple particulars and I got a fairly confident “okay” out of him after a few minutes.  I jumped back in the car and headed off to the Italian restaurant for my finale.  When we got there, I asked the matradee to have the waiter bring the ring out at the specific time I signaled him to. I ignored him when he asked if I was going to buy a nicer ring later and went to our table. We ordered our dinner, and I started talking about life and how great it would be if we were always together. She was playing hard to get and trying to change the topic all evening. I got a little irritated and finally made my move. I said, “Look, you and I seem to get along just fine. And if I don’t get married in the next month I have to go back overseas again.  So do you want to marry me or what?”  Just then, the waiter brought the ring over and whispered that I should get down on my knee and try it again. So I repeated the question again, this time on one knee and with the ring extended towards her.  Of course she said “yes” and the rest is history.  So you can see, it’s all in the planning.  Good luck and let me know how it all works out for you.

Sincerely, Dear Crabby.

Stuck in a rut? Got a question? Ask Dear Crabby, he can help!

About Dear Crabby

Stuck in a rut? Need some biased advice from a crabby old baby-boomer? Read regularly by thousands and loved by some, Dear Crabby answers questions weekly to life's challenges. Send him a note at

Speak Your Mind