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Should I cancel the trip or go for it?

Tagged as: Dating, Friends<< Previous question   Next question >>
Question - (30 July 2011) 2 Answers - (Newest, 31 July 2011)
A female United States age 30-35, anonymous writes:

Okay so, I have had this crush on this boy for quite a while - but it was an innocent crush, more just from afar. I went to high school with him, he was two years above me. It never even crossed my mind anything would happen because we were just friends in passing. But a few months ago, we ended up hanging out/hooking up. Im incredibly picky, but we just sort of clicked. It was the first time I hooked up with anyone sober. Oh, and we didnt have sex. I dislike opening up to people, thus never get very far with people I like. (I barely even like anyone anymore).

Anyhow, we kept in contact after I moved away for a few months. I always entertained the idea of us getting together when I came back, and he sort of perpetuated that idea. (Not saying we'd get together, but continuing to flirt). We lost contact, it seemed like too much work and I got scared. Now Im back and nothing has changed. I mightve thwarted any of his attempts, I mightve sent the wrong message. Or he may have just lost interest.

Recently though, he asked if he could come on this roadtrip with my friends and me, back out to where I live. Well, my friends ended up unable to go so I figured I would just get a flight out. But since I really like him I thought we could go on said roadtrip together. The thing is, he would end up living with me. He is pretty low on money and wouldnt be able to pay all the rent but would contribute what he could, and get a job when he got out there. Im fine with this, Im not one to judge and would help him out knowing he would do the same.

The problems with this are obvious. For one, he doesnt know yet it would be just us. I have a plan to tell him this though, leaving the option open to not go, making it not awkward if he feels too pressured. My friend says Im bending over backward for him, if we were just friends. I know I like him but Im not sure Id want him as a boyfriend? That might just be because I am afraid of commitment. But the only reasons he would want to come is - he wants that or he is just using me. Ive known him forever and know he is a really nice guy. But Im afraid that this trip could end in ruins.. or it could essentially change my life. I dont want to forfeit this trip because Im afraid though, I dont want to miss this chance.

View related questions: crush, flirt, money

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A female reader, Moo's Mum New Zealand +, writes (31 July 2011):

Moo's Mum agony aunthttp://www.dearcupid.org/question/he-is-one-of-the-best-people-i.html

This is the same person No???

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A female reader, Moo's Mum New Zealand +, writes (31 July 2011):

Moo's Mum agony auntThis post sounds mighty familiar. See my orginal answer which advised you not to do it.

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