Why buy the milk when…


Hi David,

Thank you for your time!  I have been dating my boyfriend for 5.5 years, and we have a great, healthy relationship… except for the fact that we are not engaged or discussing marriage plans, and I am finding this is becoming an increasingly worrisome issue for me.

We began dating when I was 20, and he was 19- and were still in college.  We always talked about marriage between us in the future, but neither of us were interested in that until after we graduated and landed jobs.  I graduated first, moved home, found a job right away and started working.  He graduated in June 2009, but unfortunately faced a poor job economy due to the recession and did not find a job until March 2010.  I assumed once he found a job we would become engaged shortly thereafter as that had always been the plan, but once employed he quickly told me of his “dreams” to purchase a new Camaro car that he had always wanted.  I mentioned my disappointment, and he told me once he purchased the car he would purchase a ring for me and we would be engaged.

My boyfriend purchased his car in September 2010, and began hinting at a ring, but 6 months later there was still no ring purchase, or any actions to convince me he was saving towards one.  Especially frustrating was he had chosen to live at home with his parents to “save money” where he lived (and still lives!) rent free.  Surely saving for a ring (approx.. $3000) would not be that difficult, especially since he has a well-paying job in the IT field.

More months went by with hints that a ring was “coming soon” but nothing.  In October 2011, he took me on a nice vacation to Kauai, HI- he paid for everything- and mentioned about a month before we left he planned on proposing there.  Everyone- including myself- thought for sure this would be the time we would be engaged!  However, upon arriving in Kauai he told me not to expect anything because he wasn’t able to save enough money in time, so there would be no engagement.  He then said to expect something around the Holidays.

Clearly, he did not propose around the holidays either.  In fact, another 6 months have gone by and we are still not engaged.  While I love this man, I also want to be realistic- is this just not going to happen for us?  He has always been very honest about marrying me, wanting to have children with me, etc. but of course we actually have to get married to make all of this happen.
I have been very intentional about not “nagging” per the advice of my Father, so I know he is not getting any pressure from me.  At the same time, it’s becoming increasingly difficult to hide my disappointment.  I’ve also chosen to not live with him, as I don’t want to give him anymore reason to postpone an engagement.
He is still living at home with his parents (now he is 25, and I’m 26), and I do know he has about $5,000 in savings.  I thought this would be going towards a ring in the near future (he even said as much as “My $5,000 is going to buy you a really nice ring!”), but now his more recent conversations over the last few weeks have been about purchasing me a new bed because my mattress is quite old (but fine!) .  

Do you think he is stringing me along? Do you think he has any intention of ever marrying me? How long is too long to wait? As I approach my 27th birthday this summer, I can’t help but think I’ve dedicated almost my entire twenties to him, and yet we are still not married and this is something that is very important to me.

I apologize for the long saga, but appreciate your insight and advice.
Thank you!



I think you are being strung along. I would suggest the following. You clearly let him know that if you aren’t engaged by a certain date then you are moving on. This isn’t a threat to him it is simply information. It’s all about staying stuck or moving forward. I would say you are stuck right now. He seems content and you are discontent. Be clear in the conversation you have with him that this is not about you threatening him. It is about what is best for your future. I don’t know the maturity level of your relationship so he may view it as you trying to manipulate him. This isn’t about that and you NEED to be very clear with him on that. Once the the ball is in his court then you follow through on what you have said and move on. The thing that will stop you is your emotion. Yet, I think it is very important what you have said, you have devoted much of your twenties to him. What is the outcome? Not what you have hoped for.

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