I'll try to make this a brief as possible. But it likely won't be. I'm supposed to propose on Friday, but am now having second thoughts. I need to make a decision. A lifelong one. And I need some serious advice. Time is running out.

The Beginning

My girlfriend and I have dated for 5 years (on and off). She's 26, I'm 33. She's kind of what you'll call "a handful". When we first started dating and she was 21, it was a disaster. She had just broken up with her x-boyfriend, and she was dating all other kinds of guys. Eventually she told me she wanted to date me exclusively. I agreed. After that things got better. In fact, they were great. We dated for 3 years. During that time we had minor arguments on and off, but overall things went smoothly. We had tons of common interests, liked going out together, etc. We did almost everything together, had common friends, things were great. We used to laugh at other couples who had issues and say we were glad that we didn't have drama like that in our lives.

The Beginning of the End

Eventually she moved in with me. Shortly thereafter the relationship became a nightmare. We started fighting often. She would go out till all hours of the night with her friends. Hang out in bars with guys I didn't know. When I questioned it, her response was always "Why can't I have guy friends?". For some reason I didn't trust her. She was overprotective of her phone. Mistrust grew, and we fought constantly. We always made up, but there were multiple instances where she would send/receive texts late at night and be out with guys in groups. She always claimed she had the right to do what she wanted and feigned innocence in doing anything wrong. I never caught her cheating. But it didn't matter. The trust was gone on my end. We would fight, I would think about how badly I thought she was treating me and I would tell her I didn't want to be with her anymore.

After months of fights, she moved out. Immediately after moving out she constantly called me and texted me telling me she was miserable, she wanted to make it work, etc. We tried dating with her living separately. Again, there was so much mistrust; things would happen where she would be out with her friends, would get drunk and never answer her phone, etc. One night, I caught her texting someone in her phone with a man's name. She refused to show me the message. She claimed, I didn't trust her and it caused a huge fight. We stayed together and worked things out. I never found out the truth. A few months later she went away on a vacation with one of her girlfriends; the whole time telling me she loved me, etc. The next day she came back and told me that she needed time to do things for her, etc. That she wanted to still see me but didn't want to be in a relationship.

The Breakup

We officially broke up. The break up devastated me. I tried to date others but couldn't find anyone that remotely compared. She would text me on and off telling me she missed me and that she wished things could have been different. This alternated between her texting me to insult me when I tried to initiate not speaking to her. I suspected (but to this day can't confirm it) that she may have been having a romantic fling with a co-worker that was also her supervisor; who happened to be married. One day I called her on it and she claimed that they were "friends" and that "nothing inappropriate ever happened". I gave in to seeing her on two occasions during the break up, on both I told her I didn't have a desire to date her unless we were exclusive. She left both times crying, telling me she wanted to date me, but didn't want to be in a relationship.

After the last incident we didn't speak for over a month.

The Reconciliation

Then, one night I saw her at a party. Instead of being mean, I was simply nice to her. She was a little intoxicated, and followed me around all night. Telling me how much she missed me, loved me, etc. The next day she told me that she knew I was the person she wanted to be with forever. That she had needed the "breakup" to realize this. That she wanted to date me again.

Cautiously, I agreed. I was hesitant from all the prior mistrust. But chalked her actions up to immaturity from ages 21-24. I also said that I was going to put the past behind us and let bygones be bygones. The first six months of dating again were great, for me. But then I found out that she was texting other guys, again. I could never prove she was cheating, just talking to them. Or making plans to hang out in groups. Apparently they were guys she may have dated when we broke up that she was still talking to. She claimed that they were "just her friends" and "that she was allowed to have guy friends". Or, that she was "texting them to meet up so that she could try to set them up with one of her friends". Throughout this whole time, however, she kept telling me that she wanted to be engaged to me constantly. The mistrust on my end continued for months. We were supposed to be back in a relationship (a serious one) and she was supposed to have realized that I was the person she wanted to be with. I could tell, however, that she wasn't telling anyone but her close friends and family that we were back together. When I saw her Facebook page she had 0 pictures of us and didn't have her status displayed as "In a Relationship". When I asked her about this, her response was "I'll display my status when we're engaged". The distrust on my end and battles continued. Primarily because she is such a stubborn person. And because I'm likely oversensitive and like to dig into things too deep. This went on until November. Incidents happened where she would refuse to drive to see me from her new place (we then lived 30 minutes apart); and her telling me "after this many years, I'll see you when I see you". I told her if she really wanted to be engaged to me, she should act like it. Her response was usually, "I acted like it before and that got me no where". The struggle continued. Me wanting her to act a certain way and her refusing to do so asserting that she was scorned in the past and it got her nowhere before.

The Way Things Are
In November, things suddenly changed. Not with her personality, because she's always been difficult. But with us. The constantly complaining about dating for five years and not being engaged continued, but she started doing things that actually made me think she wanted to be in a relationship. The being secretive about her phone stopped. Or at least, she wasn't acting sneaky about it anymore. She put pictures of us on her Facebook. She stopped going out to bars and drinking all the time. She wanted to spend all her time with me, etc. So, for the past five months things have been great again. So great that I actually started to think that she was ready to settle down. I knew I was. I figured, after five years, it may finally be time to give in to the constant complaining about not being engaged. And on my end, I'm ready to settle down. So, I bought an engagement ring. And planned everything for a proposal for this Friday.

Then yesterday morning, she picked a fight with me. Apparently, she was having a bad day at work, and I said something along the lines of "sometimes you're difficult" in response to something she said. Which led to her typical defensive and B.I.T.C.H.Y response; to me telling me she's never going to tell me anything bad again. This turned into a whole conversation about the stresses in her life and apparently her #1 stress is that she is not engaged. And that after five years, I should have done it by now and that if it were her, she would have just done it. Basically, she said, we better be engaged by next month "or else".

So, despite her rant yesterday, my plans have already been in place for Friday. But now, I'm having second thoughts. Don't get me wrong, she may come off like an awful person in this post. But she's not. She's just very difficult. She doesn't put up with bs, she doesn't take flack and, yes, she sometimes acts like the world's BIGGEST B.I.T.C.H. but that's just how she is. And, on my end, I'm definitely more conservative and willing to give in. But I'm no saint either. I'm sometimes difficult to deal with, etc. After dating her for five years though, I know what I'm dealing with and I've known what I got myself into. And in some sense, she's right. After dating for five years, she should be engaged by now. But I've been hesitant to pull the trigger because it's hard to not be concerned about the way she has and sometimes does act.

In an ideal world. We'd all be perfect. And my future wife would have done everything perfectly, we'd have never fought and there would be no doubts. But I've accepted that is just NOT reality. We're human, we do things and we make mistakes. All things considered and from what I've read on this board, I guess things could be much worse. What I need to decide is despite me wanting to spend the rest of my life with this person. Is it the right decision? I am almost certain she has done MANY things wrong in the past. But am willing to move past that; if she will NEVER do any of those things in the future. It's a difficult situation, because she's such a huge part of my life and almost PERFECT, but there are just a few things about her and that's she's done that make me hesitate and worry that I'm making a mistake.

I made a list of PROS and CONS:

Pros

She makes me happier than anyone I've ever dated. When things are good and we're together I'm the happiest I've ever been.
She's the most beautiful girl I've ever seen. I honestly have never met anyone else I'm more physically attracted to. And will likely never find anyone as I'm attracted to. Trust me, I've dated many girls in my 33 years. She is your definition of the "trophy wife".
She and I have an unimaginable amount of common interests; we love to do all the same things. Literally, everything. I've never dated anyone, I've had so much in common with.
At 33, I'm not getting any younger. I want to start a family and am ready to settle down. I know this shouldn't be a factor, but it is. I can't imagine going back to the dating and bar scenes. I have friends who are divorced and have gone out with them and I HATE it.
Her family is great. They love me and I think of them as even closer than my parents. I honestly could not ask for a better set of parents. I'm not sure how they could be so loving and caring and their daughter could be the opposite.


Cons

She's selfish. She often seems to only care about herself. If there's something that I would like her to do that will put her out, there's a 99% chance she won't do it. She's always been difficult like this.I always put her before me, in everything I do. She doesn't do the same.
She's a B.I.T.C.H; in every sense of the word. At 26 I had hoped she would grow out of it. She hasn't. She's still spiteful. She still picks fights; not just with me but with her friends, etc. She definitely has an attitude problem and you don't want to be on her bad side. Everyday I hope she will grow out of this. And in some sense she has grown up a lot since 21. But there is still A LOT of room for improvement. Part of me is concerned she will always act this way. I try to tell her to "be nice", but she laughs and says she has always been a "B**ch" and likely always will be.
There's still trust issues on my end. While I trust her now and know that she wants to be with me and is not doing anything deceitful. I still have the thoughts in the back of my mind about what she did in the past. I try to convince myself that she was young and needed to find out what she wanted. But then again, what if her actions in the past are an indication of what's to come in the future?
She may be a gold digger. She, and her friends, are a little obsessed with money and possessions. She is in debt and makes very little. I, on the other hand, make a very good salary. Not millions but very good. Because of this (and because of what her other friends got) she thinks she deserves a VERY expensive engagement ring. And has made comments, that if it is less than a certain amount she won't accept it. This concerns me. Yes, I want her to have a very nice ring. And, I would want a nice ring. But when I gave her the option of paying off all her debt and having a smaller ring. She always chooses the larger ring. Some of me thinks she wants to marry me because she thinks it will benefit her financially. She has made comments to me about how she can't want to get married and have kid so she can quit her job. I am almost certain her life aspirations are to marry someone very wealthy and have him shower her with gifts, etc. While I can provide a very good life, I don't know if it will ever be up to these standards.


In the end, I really do love her. I would do anything for her. And, if it were up to me, we would never have any problems. I could honestly spend the rest of my life with her; be faithful and grow old with her. She makes me unbelievably happy. But she also makes me miserable by the way she acts and what she has done in the past. As a result, things could be great. But they could also be a disaster. I am extremely picky and always over analyze things. Time is honestly running out and I need to make a life changing decision. I don't know what to do. My heart says you can make anything work. My brain says, don't be an idiot.

If you have any doubts, don't do it.

Trust me -- I know.

If you are having a hard time committing to a girl you have been dating for 5 years, then you should have been long gone already. I doubt she changes much after an engagement, and you have enough of a preview to know whether she is worth the risk. No matter, she will dump you any way if she doesn't get engaged soon, or if you bought a cheap ring.

I didn't even read your post. Not because I am a jerk but because I didn't have to.

Anyone who puts this much into writing about the doubts he has and explaining the situation isn't ready to make this commitment. Plain and simple!

P.S. Pro's and Con's are a huge giveaway. One should never feel that need to sit and contemplate the s/o's pros vs cons.

Your girlfriend isn't a $40,000 automobile you're trying to justify buying. She's suppose to be the car that as soon as you walk on the lot you know you're riding her home (not meant to be sexual ;)) If she's not then walk away. If you don't that salesman is going to get you!

Being engaged, or getting married, or reaching those goals, for whatever reason, is, or should be, the natural result of a relationship that has a good, solid footing.

What that is is trust, communication, respect, mutal goals, compatible personalities, and friendship. You don't have to prove yourself, you don't doubt your relationship, and the trust and communication particularly, sees you through the rought spots. Which we all have.

Love is not 'proven' by the size of a ring, nor can the event itself be dictated- or else. Love is also not bullying or demanding or selfish. Love is what you do and show, each to each other, that you can count on day in and day out. It's putting the other person's needs above your own, and being considerate, and kind. It's working through difficulties and arguments with respect.

After reading what you have written, I get the impression that if you don't come up with that BIG ring, she's going to walk. While you say she has changed a little bit, and matured some, I don't think enough time and effort has been put in by her, to have you feel confident of a lifelong commitment. With her moods and demands, in my opinion, I would personally not consider her marriage material.

Please put off the engagement, and tell her why. There are too many problems to work out, you aren't sure of her motives, and it would be unfair for you to marry her, knowing you have doubts. You are simply not ready to make this commitment. YOu don't need to apologize for being honest, and she should respect that.

If she sticks around after not getting what she wants, and works at growing up a bit, being more responsible, and less demanding, and shows more respect and dedication toward you, then I would give it another six months to be certain that she is the one you want to spend the rest of your life with.

Your brain's got it right'don't be an idiot' is an apt way of putting it.

Pros and cons lists is what I make when I consider breaking up with someone,not when I'm about to get engaged to them.

She sounds bi-polar and this is something that isn't curable but is manageable. However, it will be difficult to be with someone like that. Can you live with someone like that? It's okay to admit you can't - not everyone can. You will always feel like you will never meet someone else when you break up. But these feelings are normal and you WILL meet someone else. I agree with the above, if in doubt - don't do it. It sounds like you don't really want to anyway, you're only doing it for her because you think it will make her happy. It won't, she'll just find something else that's wrong.

I say cut all contact and move on. She's making you unhappy and I don't think you two are compatible.

Thanks for your responses. It is a very difficult situation, as I love her very much, and whatever I decide will drastically alter the course of my entire entire life. The clock is ticking and I'm pretty much past due. She brings up how she wants to be engaged every day. And, I've got until tomorrow to pick up the ring. Or, I forfeit a considerable deposit.

She truly does make me happier than any person on this planet; she can single handedly make my day great or miserable. And, I really believe that we could have a great life together and I WANT (more than anything) her to be my wife and the mother of my children. And, to her credit, she's been great lately and has not given me one reason to think she's doing something deceitful. But for some reason, I DON'T TRUST HER! But, maybe it's me and I can't get over her track record. Or, maybe I'm overly paranoid?

There are things about her that are wonderful and everything that I've ever been looking for. But then there are things that I don't agree with about her personality and disposition. She's mean. She's overly concerned with money (She says things like, "you should marry for money not for love", and I honestly don't know if she's joking or not?? ). And she has treated me like s**t in the past. I hate to say this, but she's genuinely not a good person. Although, who am I to judge. I haven't exactly been perfect. And maybe she's changed?

One day I'm ready to do it, as I can't imagine my life without her. And, the next day, I'm positive that she will take the ring and 1/2 of what I've got and do whatever she pleases then trade me in as soon as she finds someone better or with more money.

Maybe it's not the right thing to do, as I know everyone says you should have 0 doubts when you get engaged. But maybe I'm being too sensitive about things and I should just do it and plan for a long engagement. If it doesn't work out, I'll be out 35k on the ring (yes, that's the real number, I know; idiotic, but I make close to 200k a year) as the second I pick it up I won't be able to recoup any of that cost. But I will at least have tried.

Why would you want to be with someone who you think' genuinly is not a good person'?

Someone you don't trust...

Well, I've been convinced up to this point that maybe I'm just over sensative and too critical. That she's been great recently and has matured. Everyone deserves a second chance. I've made mistakes, we've all made mistakes, who am I to judge?

So, last night the SO said she was going to go out with some co-workers after work for drinks. And that she would definitely call me when she got home around 10-11pm. We live separately but have plans to move in together in a few weeks. 11 o'clock rolls around, no call. Midnight rolls around, no call. 1am, no call. I decided not to do what I would usually do, and call/txt her upset that she hasn't called yet. So I go to bed because I'm supposed to pick up the ring today.

I wake up this morning to discover a missed call at 3am. Then I get a txt at 8am saying that she was sorry she didn't call, she drank too much, passed out and didn't wake up until 3am. So from 6pm to 3am (or whenever she allegedly passed out), I am suopposed to believe that she didn't have the wherewithall to txt or call me once - because she was too intoxicated? She thinks this is fine and normal. And states that she didn't do anything wrong; "it's not like I was out with some guy"; "i just drank a little too much".

She wants me to spend 35k on a ring and spend the rest of my life on someone who can't even manage to call or text me when they said they would? Am I being unreasonable?

Is this the kind of behaviour you want to have to accept in the years to come?

What would you advice a friend in your situation?

I would advice them to break up with the person.

Sorry,Cinci,the red flags are too many to count.

Incidents like this are the exact reason why I have doubts. But, I can't help but feeling, I'm being too critical and unrealistic. What if she did honestly did pass out? She did call me when she woke up at 3am? And, she did apologize in the morning. Why do I feel like I am making excuses for her?

Of course this is the exact type of thing I am talking about. It is so borderline that she, and in turn I, am able to rationalize it; as no big deal. Yes, passing out and not calling, could be something very innocent. In fact, I think even I have done it at least once in our relationship. So, I feel like a prick saying something like this could be a deal breaker.

Because the real issue, is I don't trust her. I think, maybe she's lying. And she was out with another guy? But I can't prove it. If that were the case and I had evidence then I could have ZERO issues walking away. But instead I have her apologizing, telling me it's not a big deal, claiming nothing's wrong and acting like everything is great; in her mind we should be engaged already? But instead, all I have is hurt feelings because she claims I'm someone she wants to marry and then I'm not important enough to call when she says she will? And I feel like a jealous psychopath?

I wish I could figure our if she truly is awful or I'm constantly searching for reasons to sabotoge things and it's something I just need to get over?

Either way, whether its her, or you, you better figure it out before you commit to a future, because as it is, you make a lousy partner, and can't work together under those circumstances.

That's a shame after 5 years. Maybe you both are forcing something that just ain't happening.

That's why I'm here. To figure out if I'm the one that needs to change. Or, if it's her. So what do you think? Am I too uptight and should let things that happened previously and last night pass? Or, am I just a doormat for her to do whatever she wants?

This breaks my heart just reading it.
There are so many amazing women that you can give such things too. Women who don't need or want 35K ring to know that you love, adore, and will be with them always. I think you know the answer already. This women is not for you, and I understand at 33 its hard for you to believe that you will find someone else you will love, but I think you need to end this relationship, take time to heal from the pain, and truly see what others can give you.
I really am sorry you are going through this. I hope that even if you do marry her, it will not cause you more pain and suffering. I am sure the pain and hurt is so great now to leave but maybe that is what is truly needed for her to understand that at 25 she needs to start being an adult and understand what you would give her no matter what.
Oh this is just so sad.

Be well, and I wish you the best in all.

If you both can't change through compromise, I don't see the point in going further. Its your risk to take and the pressure is on you to take the risk. There are no guarantees of future happiness!! Seems she has given you an ultimatum, after 5 years, and you still are resistant, well she seems to have total control, so you make a decision and follow through with it. Honestly, I see no communications between you that would make me even consider taking a risk.

Doesn't matter if its you, or her, it could be you both for all I know, in which case, don't do it because its obvious you don't want to. More to the point, you are to confused to even make a decision to get engaged after 5 years. What would you advise someone in that position.

If you want to buy time, ask her to sign a prenuptial agreement, and have your lawyer cover your ***. An engagement is nothing because depending on where you are, you get the ring back if there is no wedding.

More so, after I read the pro and con list, I would have been long gone, and think you are with her for the wrong reasons anyway. Yes I have been hesitating to tell you to just leave her alone, and think you can do better. But this is your call not mine, but when in doubt, move on. You have to live with this trophy wife, and build a life with her, and so far, you can't even decide whether you want to be engaged to her.

None of this sounds hopeful to me.

Look again at your own pros and cons list and the descriptions you have submitted about her behaviour. That is who she is. Not just the positives. She has some things you like and some you don't. Bottom line - that's what you're signing on for. You can't ignore or change the things you don't like.

Wouldn't do for me, but your choice. However, you have to base it on how she is now, not how you perceive she could be. If she doesn't see anything wrong with her own behaviour she is hardly likely to change it is she?

I have to ask how on earth not being engaged is a stress, or why a large ring is required? Getting engaged and married is what you do when your relationship is great, and you want to put the seal on it and commit to the future together, because you both want more of the same, a life-time of more of the same. It's not something that fixes anything that isn't right.