So, I'm a 25 year old female living in Chicago and I've been dating someone for about the past 7 months. We dated in 2006-2007 and it ended in a horrible break-up. Mainly because I was young and immature and he is older (8 yrs my senior). To give the full details, we began dating in August 2006 and 3 months in to it, while checking my email on his PC (original intent wasn't to check his) but his email popped up instead of mine when I wrote in gmail.com and an email that was about me popped up and detailed that he had been sleeping with other women he told me were his "friends". I decided to forgive him, but in the following months, I became more and more insecure, always questioning him and not trusting him. I admit to faking myspace profiles (back then, definitely not now) and other shady things to get him to admit to things I was wondering about, versus just asking them myself. I know, I learned a lot from that whole situation and have since admitted to him what I made up was was dishonest about.

Flash forward to August 2009 and he makes contact with me out of no where, asking me to meet him at a bar. I agree to go out of pure curiosity because we hadn't been cordial for years. Things were oddly normal and the same, like I had just seen him the day before. Foolishly, I went home with him and we started to date again...

A couple weeks after our reunion, he went to NYC for business and I found out that he visited a girl he had recently dated in CT, and didn't tell me. He said he needed closure. He said they didn't sleep together but were affectionate. I guess that means kissing, holding hands and stuff. I forgave him given the fact we had just reconciled. In the next couple months, he told me about a friend that was visiting from college and she asked him to go to brunch on a Sunday. I, of course, said that was fine and later I found out he dated her about a year ago or so and actually accompanied her on a trip to Italy 2 years ago (because her original friend bailed) where of course, they hooked up the entire time. I haven't been able to get over that one and this has caused me to question his actions when he went to NYC.

2 weeks ago, we went to Puerto Rico together and it was a great trip. We have been fighting more about my not being able to trust him and it has come to surface lately that he can't let go of trusting me (bc of the stuff I did making up profiles in 2007). He left on a trip with a friend to Morocco last Friday (2/19) and told me he didn't see a future with us even though he has told me repeatidly he can, and that us not trusting each other and refusing to move on won't ever make this work and he thinks there's been too much damage. He thinks we should end it because he is 33 and wants to find who he's supposed to be with and that's not me. However, he wants to think about things while he's gone and what he wants to do but to not expect he comes back and wants to work on things. Then, he sends me an email on Sunday after being gone 2 days to tell me he arrived okay and that he misses me like he knew he would. Now I'm in this state where I hope he comes back and says he wants to work on us but keep getting upset and mad at myself for wanting that and I pretty much know he's going to come back and say that he doesn't see a future with me still. It breaks my heart because I've tried so hard to make this work and get past certain things. I need advice from people that haven't been involved in this situation on what I should do when he gets back. Is it worth sitting down to talk if he's going to say the same thing? Should I even want to work on things on the slight chance he does want to work on things to? I've been a wreck this entire time he's gone (he gets back the 28th). I can't sleep, don't want to do anything, feel lost, mad, sad, angry, alone, all of that. I need some words of wisdom...

Of course. It seems like this guy is playing mind games with you- manipulating, controlling. On top of that he seems somewhat bipolar, and clearly doesn't know what he wants when it comes to a relationship with you.

It's normal to want to have a boyfriend, but you should ask yourself some pointed questions: Are you just lonely? Are you looking at this with your feelings, or with your head? (remember our feelings are oftentimes deceptive... )Why would you want to work this out? Would he be willing? Is this a guy worth waiting for, and pursuing? Is this man husband material? Can you completely forgive and forget all the cheating and distrust that went on?
If this relationship continues, it is highly unlikely that it will ever end up healthy, especially when he keeps changing his mind on what he wants, and you cannot truly trust him.

After years of drama, heartache, lonliness, and an unhealthy relationship with this same man, I suggest putting this to rest once and for all. When he returns, I advise you: do not contact him. If he contacts you, tell him that you are moving on for your own sake, you can no longer wallow in this mess... Then go no contact. It may be painfull for you, or it may be liberating. I wish you ever happinenss and the best of luck, hun.

Thanks for your reply. I feel like I do need to talk to him when he gets back. I thought about doing the ignore him completely thing, but I do need to hear what he has to say to move forward. I don't expect he will come back and say he wants to work this out. I said, before he left, we should see someone together, someone that's not our friends, that's not our family, but he has to want that too. I can't help but hope he comes back and says otherwise, but I just won't know until he does come back and I think that's what's driving me the most nuts right now... not knowing...

Chill out. Be patient. Do you WANT to get back together with this guy? If you do, why? And could you see it working out, not just for a few months, but for the long run, for marriage? If you don't get married, you'll end up breaking up anyway. Be true to yourself. What do you see coming of this relationship, or lack thereof?

Everyone is telling me to relax and chill out and I am trying, but I can't help think about it. I know I can't control what he says and wants, but I can't help from thinking about the different possibilities. Yes, I do think I want to get back together with him. I'm not going to beg him, but that's what I want. For him to come back and say he wants to work on it too. But that's not going to happen so I have to assume the worst and quit allowing myself to think about how great it will feel if that happens. It's just setting myself up for more disappointment.

My parents "broke" me up with my boyfriend, who is now my fiancé. I expected the worst. I imagined that he would never come back for me. I imagined that it was truly over and done with. The only reason why I did, was so that I would be pleasently surprised if it did not happen that way. I know what you mean by trying to expect the worst.

You didn't answer all of the previous questions I posed though. Are you planning on marrying this guy? How will a relationship with him end up?

Sorry, yes, I do see myself with him for the long haul. There are things about him I love and things about him not so much! But I wouldn't want to work on this if I didn't think we had something special. I mean after 2 years being apart and for it to feel oddly the same and comfortable, I don't know how else to explain that. I have to be prepared for the worst... and just hope that by some chance for the best...

Sit down at couples counseling with him. If he is not concerned about working on the relationship, he isn't worth it. You also must realize that love is commitment- since you both broke up, it's something you both need to work on.

I'm going to take a slightly different perspective, and I apologize in advance because it won't be reassuring.

You have serious trust issues with this guy. He has repeatedly broken your trust and hidden interactions with other women from you, and you've forgiven him (but not forgotten).

After a two week holiday together, he goes on another trip and tells you he doesn't see that the relationship has a future. He then emails you and tells you he misses you.

I'm sorry, but this man and this relationship are NOT commitment material.

Of course you feel 'ODDLY comfortable' with this guy - he keeps you in a constant state of distress, distrust and disarray - feelings which you've become accustomed to since 2006. Yes, these feelings are ODD, and they do not bode well for the success of a long term relationship.

I don't understand how are these uncomfortable feelings are conducive to the sense that you're in it 'for the long haul' with him. Sure, you've worked on it for 4 years but you still feel you can't trust him, and you still feel distress and uncertainty. Is this the way you ALWAYS want to feel?

I have to ask - would you operate this way in any other area of your life, continuing to put time and energy and resources into something that does not provide you with the return that you desire?

I'm playing the devil's advocate here - because I just can't see what's it it for YOU.

First, he gave you reason not to trust him. You were not being immature. Even if there was nothing going on, there was reason to suspect. As for his inability to trust you... trust you with what exactly? You took on the role of investigative reporter and invaded his personal space... something that is essential for men in relationships. But the answer is not for him to finger point back at your behavior, but to remove the underlying cause that turned you into Nancy Drew.

That said, serious relationships have no room for social visits to friends of the other gender without a chaperon. This is not a matter of trust, this is a matter of respecting the one you're with and love to never give rise to doubts about fidelity.

This should apply even to business dealings. There's a reason most affairs occur with coworkers. Significant amounts of time with other people causes feelings of gratitude, respect, trust... in other words, it's an intimate relationship. Granted, it's not a romantic relationship, but a romantic one could easily generate in the presence of these other relationship factors.

Now, it's understandable that you want him back. Even a relationship that is rotten at its core is, at the very least, not lonely. Still, he needs to respect you enough to not actively create scenarios that result in him generating intimacy with other women. It's not about trust, it's about respect, the basic building block of all relationships. And when you do find a person (possibly this person if he agrees to the above) who does respect you, you should in turn respect his personal space.

Lastly, the fake MySpace profiles and Nancy Drew behavior are never called for. If you can't trust him, there is no relationship. Validating one's suspicions is not the point. It's not what he did or did not do with another woman, it's that he behaves in a way that is inherently disrespectful to the one whom he supposedly loves.