My Story And Conundrum

I was involved with a young lady for close to three years. Like many failed relationships, this was long distance and entirely online/over the phone with a single week-long visit last fall. We were very much in love, despite our handicapped means of communication and lack of physical closeness. That lack, however, would ultimately lend itself to our undoing.

The reasons she broke things off are twofold: one, she feels that she is missing out on a part of life in which a girl is expected to date, talk about boyfriends, and have fun; this is of course a direct result of my being 2,500 miles away. Two, she feels that I am uncomfortably-older than she is at 18. These are valid reasons. I don't blame her for feeling that way, but I had hoped that she might have held on if only a little while longer, as I am in fact finally in a position to move, having graduated from college and secured an opportunity for living in southern California.

There are a number of factors at play here. I am still very much in love with her. While this is by no means the first loss of a loved one I've experienced, it is easily the worst--that is saying a lot, given that my previous breakup with my last girlfriend left a mark on me for over three years. It was a mess, and I am certain that it will take me at least that long to "get over" this girl. That said, I also believe that I am capable of winning her back given the chance to physically be around her like she deserves.

The complication: she left me and immediately began dating the brother of her best friend, who had a crush on her for some time prior. He is closer to her age, but altogether less “qualified” than I am in my own opinion. Frankly, I think he looks like an old man who has no interest in pursuing secondary education in favor of instead joining the military. Bob Dylan once sang “Get jailed/Jump bail/Join the Army if you fail” and I adhere to that idea, holding out until I’ve failed at making it on my own in the real world. I come from a military family and I do not want to continue the trend.

I am quite certain that this man would readily cheat on her if given the chance to do so without being discovered. This certainty gives way to many schemes in my mind, one of which involves having a pretty female friend flirt with him while I surreptitiously videotape the incident for any attempts on his part to score with a girl while the cat’s away. This is scummy of me, but I am not entirely a good person. I consider myself to possess a good mixture of good looks, sweet personality, and past criminal activity which blends together to make an interesting mate. That is debatable, but it’s how I see myself

Lastly, there is another factor that unfortunately affects me—or rather, there are approximately fifty million such reasons. Her father has a past that while not entirely legal, was very lucrative in the area of properties that have matured in value over the decades. One such property is worth around $160M. Given that her father despises his wife and has no plans to sit on his money, his plan is to immediately divide his money among his three daughters equally upon securing a buyer, which he hopes to do by next summer. Now having said this, the money was never a great attractant for me. My ex is a wonderful, sweet, and strong person by her own merit, but now that I am effectively out of the picture, I am reluctant to give up and move on for the reasons I’ve already mentioned and additionally because holy **** fifty million dollars. Whether this makes me a scumbag is beyond the point. I have good qualities in abundance and I honestly believe that I am good for her; she holds this belief still, based on our recent conversations, but she feels that she has committed herself to her new man. That’s where the probably-illegal plan of mine would come into action.

I am not exactly asking for advice, but I do feel that this should be said if only to strangers on the internet.