I know this is the Wedding section, but the advice here is much more helpful. So my situation is this… This girl (we’ll call her Amy) is coming from upstate NY to visit me in Massachusetts for a few days. We were great friends in college until she transferred to a school closer to home in Albany. I’m from Boston. I haven’t seen her since last November when she came to visit an old college roommate of hers (a friend of mine as well.. we have a lot of mutual friends). That night in November, I can remember driving home and getting into bed, asking myself why I missed this girl so much. We exchanged texts at around 3am saying that we missed each other and I believe that I even said I loved her. And I do.

Fast-forward almost 9 months later. Here we are in late August. Amy and I have talked everyday since her visit last in November. A lot of times she will wake me up with a good morning text and be the last person I talk to before going to sleep. In between all of this, we text each other every few hours having short little convos. It’s a nice feeling. I remember in March telling her about my feelings and she had just wanted to stay friends. Then two months later, she tells me that I am the only guy for her. I was driving at the time and actually had to pull over because I couldn’t believe what I was hearing. After she told me this, it was almost like she tried to protect herself because all I could get out of her was “idk” and “idk what I want or what I’m doing”. Having helped her get over her last relationship, I told her that I wasn’t going to pressure her. That I know she had been hurt a lot in the past and to remember that she can always talk to me. (I’m sorry for the novel. I just wanted to give you a good idea of what our friendship was like.)

We’ve said a lot of cute things to each other. Things that ordinary friends wouldn’t say to each other. About a month ago, she was called in to jury duty and had to attend from like 7am-10pm Monday thru Thursday, and toward the end of the week, she got sick. I did a little Google searching, found the closest (and nicest) florist, and had flowers delivered to her with the card reading, “Just wanted to brighten your day. Hope you feel better.” And it was of course signed by me. She loved them and started giving me more attention. Plenty of texts throughout the day that just had a smiley face in them. I was really, really happy that this was going somewhere, and I felt like I had finally gotten myself out of the friend zone if I was ever in it. I consider this girl one of my best friends and even though we’re 4 hours apart, I feel incredibly close to her. Now, I don’t know if this is with all girls, but she’s a little hard to read sometimes. The extra attention she has been giving me stopped the last week and a half. Probably because of her new job. She was out for her friends 21st birthday the other day and I woke up to a text from her at like 3:30 AM. It might be a little weird to you guys, but she does this once in a while. It makes me feel good because I know that she is thinking about me. So anyway.. the text read, “Getting pizza… I miss you.” Haha. She was probably drunk.

So she is coming to visit me on Friday. I’m picking her up at the train station and we’re going to hang out the rest of the day, all of Saturday, and a little of Sunday. I’m sure we’ll sleep in the same bed together. We’ve made little comments before such as, “wish you were here layin’ next to me.” So I think it’s a safe bet to assume that we’ll be sleeping together. As far as sex goes, I don’t think it will happen. I’m not upset about it really. If it happens, it happens. I’ll be prepared. But I just care about being close to her and spending time together. If you’ve read this far, I’m sure you can tell that I really care a lot about this girl. I hope to make her my girlfriend this weekend. Here’s my question:

Do I have a “relationship talk” with her? When do I do this? When we’re cuddling at night watching TV? I know that she’ll bring up the distance issue.. we’re only 4 hours apart. If it does get brought up, I’m going to say that I’ll visit her as much as I can. 2 weekends a month. Thatll be hard to do considering I go to college full time and I’m going into my senior year next Monday. Basically, what I want to know is, do I talk to her about a relationship? If so, what’s a good way to ask her without sounding high school-ish (i.e. “Will you go out with me?”) When should I tell her (when I’m driving her back to the train station on Sunday? In bed cuddling?)

I want to say a HUGE ‘thank you’ to anyone who took the time to read this. This weekend is going to be the most important weekend of my life and has been almost 10 months in the making for me. Haha. Thanks again.