The Bitter Single Guy's Relationship Advice

Dating and Hook-ups and Boot Camp, Oh My!

Dear Bitter Single Guy: Okay, you said you liked long…and well this is long. So I’ll start from the beginning.

4 years ago I graduated college and moved back home. I went to a women’s college and was well not so great at dating…well I’m still not, but anyways. I met this guy I worked with, a total bad boy. Hung out with him all the time, we had a relationship more or less based on sex. I tried to pretend like I had feelings for him just to make myself feel better but, that didn’t work. We stayed friends and I currently live with him. He and I barely talk at this point and most of the time I can’t stand to be in the same room as him. We’ve lived together for a little over 2 years and no, because everyone asks, we don’t sleep together. So anyways, I started meeting all his friends and his Best friend, who I didn’t really like that much went away to college. The roommate, we will call him B, didn’t go to college so he didn’t understand when his best friend (we’ll call him Robby), had less and less in common. Robby didn’t call him much and only saw him on breaks. B was not too happy with this. And Robby being a broke college student, which I fully got, never had money to go out. B got mad that he never had money to do anything and they eventually stopped talking over money. It’s kind of sad really. Robby graduated this past May. He went to school late for financial reasons. He and I have been hanging out on a regular basis ever since he moved back home. We get along great. I guess things got really close in August, we hung out almost daily. Well, I forgot to mention but sometimes when we are drunk we hook up…which this has been going on for a couple years…so it’s nothing new. Anyways, we randomly decided to go to Florida together as friends. I had vacation time and he had to get his transcripts. He had decided to join the army so this was sort of a last hurrah.

We had the best time…I have never had so much fun on a trip. He was talking to a girl at the time, and I sort of hooked up with one of his friends from college. Ever since we got back we’ve gone out 4 to 5 times a week…it’s only been 2 weeks. We text everyday and  he visits me at work. We are really close. He asked me to write him while he was at bootcamp. At first I sort of joked around about it but then he asked me on 2 more occasions. I should mention I am a writer and am working on a book and a poetry book. He told me to include my poems because he has always wanted to read them. Then he told me he was going to give me his basic training sweatshirt and we were going to go to Florida again when he gets out of basic. Again we are not dating, just friends. The whole situation is weird to me. I moved my whole work schedule around to hang out with him this weekend because he leaves on Monday. My friends think there is something going on, but at this point I hate them for making me over think all this. My roommate thinks we are in weird romantic comedy and Robby is going to profess his love for me at any second. I think this is all ridiculous. We have not had sex since before Florida. And I know for sure I am not the type of girl he normally dates. Plus he talks about girls to me all the time. I think it’s all rather innocent…am I being stupid or are my friends stupid? I’m so confused. Please Help. ~Not Sure What’s Next~

Dear NSWN: So the Bitter Single Guy isn’t sure where he said he likes long letters…on the contrary, the BSG has a short attention span and gets confused quickly. As he did with your long letter. By the way, if you’re an up-and-coming writer, the BSG recommends some time spent in editing. Someone (the roommate?) went to school late because of financial reasons? That didn’t actually drive the narration forward…the BSG isn’t sure why that was relevant. But hey, let’s not talk about editing, let’s talk about how confusing your letter was!

Seriously NSWN, the BSG isn’t sure he has all the details, but he’s going to try:

• You live with a guy #1 who you used to have sex with but who you now can’t stand.
• Guy #1 has a Best Friend (Guy #2) who isn’t in college and doesn’t understand people who are in college. The BSG isn’t sure why this is relevant, but whatever.
• Guy #2 has a roommate (Guy #3) who you’ve been hooking up with as friends and traveling to Florida with and who is now in Boot Camp and who Guy #1 thinks is going to profess his love for you (the BSG doesn’t know why you would trust anything that Guy #1 says).
• So your question is basically that you don’t know what’s going on with Guy #3, correct?

OK, if all that’s correct, the BSG thinks he’s got his head around this and has a few thoughts (in a second list):

1. Please move out of the place you share with Guy #1. You have weird history, you don’t like him and he’s overly involved in your experience with Guy #3.
2. What’s up with Guy #2? Have you introduced him to the BSG (and now his readers) and really just left us hanging? Is Guy #2 going to start college? Will he ever understand his Best Friend (Guy #1)? Will they hook up? Seriously NSWN, fill a brother in here.
3. Having sex with someone whose company you like and who you enjoy occasionally traveling with is the basis for most long-term relationships in the United States, with the possible exception of the regular sex. Call it what you want, but the BSG is going to call Guy #3 your boyfriend.
4. Guys (probably girls too) who are in Boot Camp cling to whatever romantic thread they may have left dangling when they began their Military Adventure, so the BSG wouldn’t recommend reading too much into anything he says or does during this time.
5. The Advice: Hang with Guy #3 to see what it becomes, but under no circumstances should you marry him (see point #4 above). If you need more clarity from Guy #3, have this conversation with him: “Hey [insert Guy #3’s actual name here] I like hanging out and like hooking up with you. What do you say we make it official and be boyfriend and girlfriend?” The BSG doesn’t think you should necessarily decide to be exclusive since you’ve recently hooked up with Guy #3’s friend (Really NSWN? Guy #4? Edit, edit, edit) and probably aren’t ready to settle down.

Good luck.

~BSG~

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