Propose a Tip of the Day

There is a certain biology teacher, lets just call him, em…Mr. McMillin, who has been dating his girlfriend for 8 years, four of which have been long distance. Well, he's finally ready to take the plunge, and wants to ask his girlfriend to marry him. He has a problem, he doesn't know when to do it. He was thinking of New Years Eve, but some of the ladies he works with mentioned that it might not be wise to make her wait through Christmas. After all, she might be expecting it (after 8 years), this Christmas and find herself disappointed. So now, he's thinking in order to make it a suprise, perhaps he should just go for Christmas Eve. Poor guy, all of 24 years old and so confused. Anyway, I figure, there are many avid readers of Pete & Jay's Tip O Da Day who may have some advice for this poor boy.


Jay said…
I'm staying OUT of this one. I fear being publicly scorned for saying the wrong thing!
vander said…
I vote for before Thanksgiving, especially if these kids have big families. That way, they can make their big announcement once and enjoy the whole holiday season as an engaged couple. Plus, it's a new excuse to divide extended-family visits (sorry I can't come, but we're going to HER parents' house this time, etc.). May politely point out that life-changing proposals really don't need to ride the coattails of a major holiday to be meaningful. If it's been eight years, sheesh, do it tomorrow.

And also, fall is cuddly.
Pete said…
"He has a problem, he doesn't know when to do it." Sounds like a big ol excuse if you ask me. I'm with VM, do it tomorrow, or in a couple weeks. She's going to remember it for the rest of her life. No need to wait until 2006.
Kris said…
Correct me if I'm wrong, James, but part of the waiting is to get a paycheck that can pay for the ring, and part is that you won't see her tomorrow? She's still in Boston, and though he went to visit her this weekend, he could not yet buy the ring...although, I think just before thanksgiving might be an option.
Remember, he just started his first "real" job, and he's only gotten his first 2 paychecks. Those probably went to the plane trip to see her this weekend!
CGrim said…
I vote for Martin Luther King Jr Day.

When she doesnt get it on Christmas OR New Years, she won't be expecting it at all. Plus, a proposal modeled after the "I Have a Dream" speech practically writes itself...
vander said…
Careful - at the end of your proposal you should avoid joining hands and singing "Free at Last". That's a moodkiller for sure.
Stephanie said…
James, what's going to make it extra-special is some serious spontanaeity. My friend married her husband after ELEVEN years of dating (they never broke up, and I must point out that I fixed them up on the bus in 9th grade). And let me tell you, ANYtime he planned an outing with her and it seemed the least bit more "planned" than usual, or it was a holiday, she thought she was totally on to him. She was always so suspicious that he ended up proposing in a Carraba's parking lot as she was stepping out of the car.

Not proposing after a long time isn't such a bad thing, especially since you're so young. Just know that the simple truth is that many girls over the age of 20 that are happily dating someone steadily are probably drumming their nails after five. Girls? Do you agree? That expectation is something you can't avoid, so you have to be extra-extra creative. :-)

SO, the key would be here...pick something out that you do every once in awhile as a treat. Going to get ice cream? Taking a walk in the arboretum? Making dinner together? Pick your setting, then go from there and plan something as simple or complicated (cue camera crew and clues as in one engaged couple we know) as you desire, and just be creative. She CANNOT leave the house thinking, "I think I'm going to get engaged today (unless you plan to have her on network TV, then she'd kill you because she didn't do hair and makeup)." Once she's on her way, be as secretive or as obvious as you'd like.

The initial departure should not raise any eyebrows and your goal is to NOT have her calling her friends prior to your picking her up saying, "I think he's going to ask," but have her instead calling the friends afterward telling them, "You wouldn't believe how James proposed!!"

Just so you know how said friend's husband in my story did, she called me and said excitedly, "I got my ring! it's a carat, it's a carat!" Humm, I never knew what to think of that.

Best of luck to you and make sure you let us know how it goes!

p.s.--You could always skywrite at Keeneland in October if one of your friends hasn't already stolen that one. I wonder what those pilots charge? ;-)
Jules said…
James - I fully concur with Stephanie. Spontenaity is key. And when she's expecting it around every "nice dinner out" corner, you'll have to be extra careful to have it truly be a surprise. But a surprise it should definitely be. I also agree that 8 years is not that terribly long when you consider you started dating when you were 16. It's not like you're non-commital or anything. You were just waiting to grow up. :) I stand behind you on that one James.

Vander Molen made a lot of good points too. My favorite being, "fall is cuddly." Ha. I do enjoy the thought of the entire holiday season basking in the light of the ring. Oh wait, this isn't me, is it? I'm sure your girl will feel the same - rather than hoping each new holiday will be the time you do it, she can rest secured knowing she can finally plan her wedding. Plus there will be lots of opps for girl conversations with moms, aunts, girl cousins, etc. over pumpkin pie, coffee, christmas cookies, and shopping about the planning of the wedding itself.

Dang, I wish I was getting engaged before Thanksgiving.
vander said…
I realize this is a little late, but didn't get to post at the end of the day yesterday. I have a magnificent idea for a truly unique marriage proposal. Are you ready? It's a highly complicated process, so be forewarned.
1. Tell her that you love her.
2. Tell her why you love her and not anybody else.
3. Ask her if she'd be willing to love you and not anybody else, um, forever and ever amen.

It's nice to make a big gesture, but that's really not the point. You don't have to spend any money or get all dressed up or stage an elaborate production. If you want to, that's cool. But an honest, heartfelt conversation beats the crap out of a jumbotron show any day. And (subtle reminder) fall is cuddly. God provides the ambiance; all you have to do is say the words.

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