ACTUAL LETTER TO DEAR JON:
I have been dating my girlfriend for about 5 years now and everything is good except I'm starting to feel the pressure of marriage. We don't talk about the subject much, but I can tell she thinks about it a lot, and the fact that several of her close friends have recently gotten married surely must have her wondering when I'll ask her.
The few times we have talked about it, she's gotten very upset with me, and I understand why she feels the way she does, and I know she wonders where this relationship is going. I think the relationship is great; I'm very happy with her and very much in love with her. But the truth is I don't think I'm ready for marriage; to her or anyone right now. I do think we'll get married someday, just not yet. Meanwhile I'm worried that she might get tired of waiting and move on.
Should I ask her to marry me just to make her happy even though I'm not ready for marriage, or do I hope she'll be patient enough wait for me?
Not ready yet
There are some gaps in the information that will make my answer necessarily conditional and incomplete. For example, 5 years to me sounds like a long time, unless:
a. You started dating when you were in ninth grade and you are now a sophomore in college. In that case, "waiting" may yet be a pretty good idea.
b. For four of those five years your dating was by correspondence because one of you was in prison.
I don't know about either of your citizenship status, any previous marriages or children, transgender surgeries, bankruptcies, large indebtedness or alimony settlements against you. So I am going to assume that you and she are both stable in terms of legal status, family network, sexual identity and employment. In other words, I am going to take the leap in assuming that you are a "normal guy," which leads me to one conclusion: If we were in the same room I'd cuff you on the side of the head.
Dude, five YEARS? What are you "not ready" for? To borrow philosophy from John Fogerty and the Creedence Clearwater Revival, what if "someday never comes?"
(I'm pretty sure that's what he's singing. I pick that up from my Classic Rock station in my car and I haven't looked up the lyrics because I don't have time. But I have been WAY off before on lyrics I thought I was hearing properly. Like with "Stairway to Heaven" by Led Zeppelin. After it goes metal and they sing "And as we wind on down the road," everything after that is hard for me to hear. I thought they sang next, "I sure was stoned out in the cold," which, considering what the song was about, sure sounded right to me. But that's not it. What they sing is "Our shadows taller than our soul." Now that makes so much more sense! So maybe CCR sings "Sunday revel chums," which refers to guys across generations who otherwise don't communicate very well, finding their best moments are in gathering together to watch televised football.)
Meanwhile you're worried that she'll move on. You have to know that she has approximately one million girl-friends telling her, that nice guy as you might be, it is time to dump you. The reason is that the nature of this relationship, while it might be great from the male perspective that relishes a certain amount of freedom and flexibility, is actually taking the female for granted. The woman perceives that this is so because it really is so, whatever good intentions or feelings the man might have about the status of the relationship.
This has nothing to do with men being asked to engage in telepathic empathy, or to be held accountable for our failure to multi-task our listening skills while reading the newspaper. No, on this score, women are right.
You have stated four facts: 1) It's been five years 2) You are happy being with her 3) You love her a lot 4) You expect to get married some day.
On that "some day" basis it is time to ask her to marry you. Buy her the rock, get it on her finger, and do it romantically. What she needs to know is that you are committed to her for life. The rock solves that. And then, negotiate the date. You don't have to get married next week.
However, the engagement should not last longer than eighteen months or she will see that the device of getting engaged was actually an avoidance mechanism, which will only confirm that you are taking her for granted.
Since you are looking at getting engaged in November and announcing to your families around Thanksgiving, you can conceivably claim that this summer is too soon for the wedding, and that you would like a lovely summer wedding in 2010. This all becomes even more plausible if you need to shop for a new home together, apply for a residence visa, complete your parole requirements and remove the ankle bracelet, etc.
The important thing to consider is that if she has the rock on her finger and something specific to plan on, your relationship is on solid ground again, and her friends will like you again. You need her friends on your side, especially as a wedding comes up.