Looking Up Lost Love
Find a Conversation
| Thu, 10-13-2005 - 3:56pm |
I've been driving myself and all my friends nuts with this, so I thought I'd take it to the streets. I’m 25 and when I was 17, I dated a boy I’ll call Bob for less than 4 months. We were in the same grade and I asked him to a concert because I was trying to sniff out if he had any feelings for me. Immediately, he wrote me a note telling me that he’d had a crush on me for two years and hadn’t said anything because he didn’t think I’d go out with him. Within a couple of weeks, he’d dumped his girlfriend and was pursuing me like nobody’s business. We were very hot and heavy while we dated and I’ve never before or since felt that close to a boy/man. I was the one who ended things and it basically boiled down to the fact that he was not a very motivated kid and I was. I had a job, a car, etc., and he didn’t. I felt like I was getting the raw end of the deal, driving everywhere, etc. Looking back, I realize that a lot of it was his living circumstances. For example, his parents didn’t have the money or spare car to help him out until he could get his own and without a car, he couldn’t get a job because he lived out in the country. Also, his father had a very bad temper and his step-mom pretty much used him as a babysitter for his younger step-siblings.
Anyway, after I broke up with him, we didn’t talk. He tried to get me to come back to him, but I declined. Fast forward to my freshman year of college. After high school graduation, Bob had moved to Ohio to live with his mom. He had a full-time job and a motorcycle and was generally a productive member of society. After about a year of this, he came back to the small town where we’d grown up. His mother was growing sick and refused to take care of herself, so Bob told her he wasn’t going to stick around and watch her basically kill herself. Upon his return to our hometown, the first place Bob went was my mom’s house (where I’d grown up). He told her about his time in Ohio and asked what I was up to. At the time, I was in a serious relationship, so my mom told him. He seemed upset, but hoped I was happy.
Fast forward two years. After my sophomore year in college, I took a year off to save money so I could continue my studies. I lived at home with my mom and worked two jobs. The relationship that I had been in during my freshman year in college was petering out and I was basically looking for the right time to break it off. Out of nowhere, Bob approached me while I was working one of my jobs at a local store. I was so shocked that I gave him a huge hug without thinking. He seemed surprised but pleased and told me he’d call me the next afternoon after I got off my daytime job. We talked for an hour or so and he suggested I come over to watch a movie sometime. He also asked if I was dating anyone. I told him that my current relationship was on the outs. A few days later, he called again and asked if I’d like to meet him and his cousin at a local pool hall/bar. He asked if I’d broken up with my boyfriend yet and when I said no, he asked why not. I agreed to meet him, but ended up chickening out and canceling. I knew that if I was around him for very long, I’d want to date him again. I was afraid that if I got close with him again, I’d avoid going back to college and I definitely didn’t want to do that. So, that was that.
Fast forward to now (three and a half years later). In July, I broke up with a man I was engaged to marry (rings and all) and my heart has been through the blender and back. I’ve been thinking about look up good old Bob to see what he’s up to. Honestly, he’s the only guy I’ve dated that gave much of a sh*t about me. I realize that it is entirely possible that he’s married and/or has kids or maybe he just doesn’t care about me in that way anymore. But I feel like I have to know. No matter how things turn out, I feel like any resolution is better than none.
Am I crazy to be entertaining these thoughts?

Good luck.
Okay, I dropped him a letter that was along the lines of “just wanting to see how you’ve been” and after a couple of torturous weeks waiting, I got a reply! He is in the Army and his unit is scheduled to go to Iraq within a few weeks, but he is not likely to go because of back problems that need to be resolved. Either he will be medically discharged or his commitment will be lengthened but will not include combat.
He is married, but they are separated. We have talked on the phone twice and the first time he was saying, “my wife this and my wife that” and the second time he was saying “my ex-wife,” so I’m assuming his change of terminology indicates that divorce is on the way. He stated that the reason they have separated is that she didn’t like living so far away from her family. He is stationed is about 9-10 hours from our hometown, which is where her family lives. At any rate, he seems to have had time to adjust to situation because he was very casual about it and didn’t seem upset at all, really. Overall, I feel extremely relieved to have had at least these two chances to talk with him. I was able to get things off my chest and, in reality, that was what I needed the worst.
I do have some questions in regards to how things stand now. Since I was the one who broke up with him in high school and have rebuffed him once since then, I’ve been advised by some that I’m going to have to be the one to “extend the offer” this time around. This is totally understandable and I think it’s only right. However, I want to tread lightly because A) he’s still technically married and B) I haven’t been reacquainted with him for long.
To complicate matters (like they aren’t already complicated enough) I’ve been reading He’s Just Not That Into You, which incidentally I think is brilliant. Basically the premise of the book is: guys really aren’t that complicated – if they’re into you, they’ll pursue you, end of story. If I were to follow this book’s credo literally, I wouldn’t contact him again but would rather be content in the knowledge that since he has my phone number, he’ll call me when/if he gets interested in dating me. By definition, if he doesn’t call me and ask me out, he’s not interested. In consideration of the fact that I broke up with him in high school, the book’s author would say, “Well, you broke up with him in high school for a reason.”
My crux is that it has been eight years since we broke up in high school and both of us have changed materially since then. There mere fact that he’s in the Army at all speaks volumes to me. Should I assume that I’ve done by bit or should I keep extending myself?