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Should I propose for a second time? Thoughts please!!

Tagged as: Big Questions, Dating, Friends, Love stories<< Previous question   Next question >>
Question - (24 November 2012) 8 Answers - (Newest, 27 November 2012)
A male United States age 36-40, anonymous writes:

What a god damn cliche I'm about to spew, but it's the truth and I need guidance. Girl moves next door in 5th grade, boy befriends girl. They become best friends by the summer before 6th grade and continue this sexually frustrating relationship until age 18. They go to prom together because her douche-bag boyfriend of 6 months breaks up with her two days before finally realizing she's not going to 'give it up' to just anyone. Boy is a real gentleman the whole night then girl, in her sadness, wants to make love in the backseat of boy's piece of shit F150. Boy refuses because 'it's not right like this' and he walks her to her front door at midnight and she frenches him and says thanks for being a gentleman. Boy contemplates never brushing his teeth again because he may never kiss the woman of his dreams again.

Next day, girl tell boy she's going to a university two states away. A college he applied to but was rejected. Boy spends the next 3 months trying to convince her to stay local but she refuses saying he is being selfish. They end up losing their virginities to each other on the eve of her departure. Boy refuses to shed a tear but vows to reunite with her once college has ended.

Fast forward 4 years, she moves back into her parents house while she finds an apartment. While unpacking her things, she sees boy playing video games on his own in his room. She texts boy, he comes over and they talk for a bit. She explains how she had a couple serious boyfriends in college and was almost engaged once but denied the man. She explains how she experimented a lot over the last 4 years with girls, alcohol and drugs. She said she had no idea how she graduated with a 3.9 GPA but was very glad she did. Boy tells her he had one girlfriend in college but it ended the previous year after only 2 years together. Boy also experimented with drugs and alcohol... but no men. Boy and girl have sex that first night and then start dating.

Fast forward a year, boy and girl are 23. Boy proposes, girl rejects him. She goes back to college for 4 more years for her PhD. He follows her because he miraculously got a job in the area. Boy and girl are 27 now and he wonders if he should propose again.

I've made it sound like she's the selfish one but honestly, she wanted to be independent for a while before she settled and I'm totally okay with that. Which is why, since we've been a serious, long-term couple, I've never forced her into anything. But I'm just curious, should I pop the question again? I've had the same ring in my underwear drawer this whole time...

View related questions: best friend, drugs, engaged, text, underwear, university, video games

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A male reader, Serpico United States +, writes (27 November 2012):

Just me, but any woman who turned down me asking a first time sure as hell wouldnt ever be lucky enough to find out what a second proposal feels like, at least not from this guy.

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A male reader, anonymous, writes (26 November 2012):

You have to be careful. Broaching the subject could be a turning point in your relationship. Either it could steer it towards the path to marriage or to its demise. You have to be a little selfish here. The primary function of a marriage is to raise children. Do you want to have a family? Then start the discussion. It that starts the end of your relationship then it would be a good thing for you, even if it won't feel like it at the time. If you would like a family but only with her, or you would be happy either way as long as you're with her, then let her bring it up (if she ever does).

But the choice is not whether to propose or not, its whether to discuss it or not.

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A male reader, DV1 United States +, writes (25 November 2012):

DV1 agony auntI wouldn't propose yet. She'll let you know when she's ready for marriage. Why not just enjoy her company in the meantime? You don't have to be married to love each other... Sounds like you have this whole way you want things to go instead of letting things happen as they're meant to... Just relax, what is meant to happen will happen. No worries.

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A female reader, chigirl Norway +, writes (25 November 2012):

chigirl agony auntI don't think she sounds selfish either, you gave a very objective walkthrough of the events. I don't understand why she wouldn't be engaged to you while taking her Ph.D, but I do know that traditionally you should be married within a year after getting engaged, so that could be a reason why. Getting married costs money (if you want any form of celebration). It also takes time to plan, organize, and then the start of a marriage is very difficult, I hear whatever problems you had in the relationship becomes 10 times harder, but then after 3-4 years it calms down and you settle in the new routines. Anyway, that's a lot of pressure, and probably not ideal when you're also studying. So I think it was a smart decision, you should be married once you are at the right stage in life. She obviously didn't feel it was right back then, it could jeopardize your relationship had it been too early.

So I'm thinking, yes, propose again. Now she will be finished with her studies soon, and you can get married. Although I do think you should wait a little more so she doesn't have to plan a wedding at the same time as finsihing her exams. Although, you could propose and then tell her that you should not set a date before she finished her exams, that you can stay engaged for a while before getting married.

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A female reader, CindyCares Italy +, writes (25 November 2012):

CindyCares agony aunt I don't think at all she was selfish! She was sensible. She just wanted to go to college , and to get a Phd , and she would have been totally stupid if she had sent this belly up for the sake of an 18 y.o. boy that she had kissed once, and later for the sake of a 23 y.o. boy that she had dated one year.

Now , 4 years later , it may be different. School's over, education is completed, grown up life starts for real, and you have been together 4 years, committed and monogamous.

It all depends if she wants to spend the rest of her life with you, and it's a tad strange that you know so little about her wants needs and plans, and that a proposal would be so hit or miss. As another poster says, generally an engagement ring is sort of like the seal to a deal done, and it comes after having already talked about the future, where to live, having children etc.

Do you know at all how she sees her future ? If she needs / wants to relocate for work, if her career will be local or bring her somewhere else ? If she actually wants to get married and have children ( not all women do ) ? How, where and with whom she sees herself living ten years from now.... I'd start having more clarity about this kind of important stuff, before whipping that ring out again. Good luck .

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A female reader, anonymous, writes (25 November 2012):

That's a beautiful story. Sounds like one of those "meant to be together ' type of stories.

But it could end bittersweet. Which would be part of the beauty.

Ok now to practical and realistic matters.

If she rejected your first proposal but nonetheless continued dating you exclusively I think there's hope.

Have you two ever discussed marriage while you were dating? You shouldn't spring a proposal on someone if you don't have at least a good feeling that she could say yes. People don't like being put on the spot and can feel pressured. Also it would be very awkward if she has no intention of getting married yet you're proposing as it shows a fundamental disconnect if you are on such different pages.

To me, popping the question is just a formality. By then you should already have discussed or at least started talking about whether marriage is in the cards or not and only if it is then do you go ahead and do a formal proposal at some point. The proposal shouldn't be the first time she is hearing the concept from you!

Therefore I would say whether you should propose or not depends on what your discussions concerning marriage have been like and if you have never discussed it then its time to do so without actually proposing out right but just getting a feel for where she sees her future headed and whether she would it to involve you.

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A female reader, Honeypie United States + , writes (25 November 2012):

Honeypie agony auntI would, BEFORE, you propose again, sit her down and have serious chat about the future together.

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A female reader, janniepeg Canada +, writes (25 November 2012):

janniepeg agony auntHave you ever talked about long term plans? Maybe you can start with smaller questions such as do you see yourself living with him, having babies in the future, do you believe in long engagements?

Now she is finished with her Phd. Is she established in her career or will she still be moving around for her job? Within a serious relationship, is she devoted to you or is she kind of busy? Will you be satisfied with her, knowing that she is an independent soul? Does she make you feel like you are a priority?

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