Quick background: I’m late 20’s, never asked a girl out before (have social anxiety, working on it). It wasn’t until recently when I realized that there was a girl in high school that kept dropping MASSIVE hints that she’s into me. She recently messaged me on Facebook and dropped yet ANOTHER massive hint that she really wants me to ask her out.
Blah blah, two weeks later, judging by our lengthy conversations, I can safely say without a doubt that if I were to ask if she wants to go on a trip to Australia with me, she would definitely say yes. Both her and I have always wanted to go to Australia and this seems like the perfect thing to do. So I’ve decided that I’m going to do it.
- If I ask her to go on a trip with me to Australia, is she expecting me to pay for her airline ticket (I’m totally fine with paying, I’ve been saving up money and am totally fine with blowing it on this awesome trip)? FYI: She currently lives in China at the moment while I live in USA.
- Hotel situation: do I pay for her hotel room? two separate rooms? One room for both of us but two separate beds? One room one bed?
- Side question: is she expecting sex on this two-week trip? I’m still a virgin and I don’t think I’m ready to immediately jump into that, but I want to mentally prepare how to tackle this situation should that subject arise (most likely I’ll turn it down and tell her I’m a virgin).
Any help would be appreciated!
It always fascinates me that the guys who are admittedly the worst at dating always come up with the grandest gestures as pretexts for flirting, hitting on women, or trying to secure dates. I wish I knew why so many guys who are in similar situations like you do this. Socially awkward or suffering with social anxiety, very inexperienced, earnest guys who just want to find some way to connect. You guys always ask the “What if I took her on a hot air balloon on the lava planet Mustafar?” type of questions instead of “What if I just ask any girl on a date and do that until I build confidence?” question.
I say this as much as possible but it always bears repeating: I’m not a mental health professional. I think this is important to say when people mention things about themselves that could be interpreted as them just being hard on themselves, or actual mental health issues. If you have crippling social anxiety, seek professional help. If you just get anxious around people but could get better at social interactions through practice, do that. It sounds like you might fall into the “I just need to get comfortable” space, since you’re planning a giant trip with huge social obligations. I could be wrong, but I’ll just assume that’s the case. So, since I think you’re more socially inept then in need of professional help I’ll be frank: This is a terrible idea and I refuse to entertain it or give you advice on how to pull it off.
You need to get over this “Nice Guy” thing you’ve got going where you feel like it’s perfectly normal to pay for someone’s flight to Australia on a whim. You aren’t rich and you’re willing, in your stupidity, to pay for someone’s international flight because….why? What is even the point? Same goes for the hotel. Are you kidding me with this? Why would you pay for all this? If your answer is “It’s the nice thing to do” I will LOSE MY SHIT. Stop it. I have no clue what you’re hoping to accomplish by paying for a high school friend’s flight and hotel for a trip to Australia, and I don’t think you do either. You aren’t trying to sleep with her so…what do you hope to get out of this? A good time? Fun in Australia with a friend who you haven’t seen in years who recently started hinting that she might be into you? She doesn’t even live in the States, so it’s not like you can build a real relationship with her after the trip is over. I want to be crystal clear when I say this: THIS IS A BAD IDEA. DO NOT FLY HER TO AUSTRALIA. You can invite her to Australia if you decide to go on your own and she decides it’s worth paying to meet you there, but even that is pushing it. Again, you must have a reason for wanting to arrange all of this other than “We’ve both always wanted to go”. You aren’t her husband trying to redo your crappy honeymoon, you’re a guy she went to highschool with who chats with her on Facebook. What do you hope to accomplish here other than putting yourself in a weird situation where you’ve paid for a quasi-friend to meet you in a foreign country? Sorry but I think going on a romantic trip with someone you aren’t close with, who will probably assume there will be sex when you’re clearly not ready, aND who you have no hope of building a real relationship with is a bad idea. So stop even considering it.
Look, I understand that sometimes it’s easier to make the grand gesture with someone you don’t know all that well than it is trying to connect with new people. You must really have trouble connecting with people if you think that the “Perfect” way to connect with someone you haven’t seen for a while, who you’ve been messaging on Facebook, is a trip to Australia. That sounds like a desperate move, and maybe that just seems easier to you than just approaching a girl at a bar and saying “Hello, my name is Chad, nice to meet you”. Seriously though, that’s what you should be doing right now. You shouldn’t be trying to reconnect with a friend from High School who you have romantic interests with, to take her on a trip to Australia for two weeks, to hang out together and then part ways with her going back to China and you back to the states. You can connect with her, that part isn’t the issue, but going on a trip to Australia (or worse, paying for her to go on this trip) as a pretext to take her on what would essentially be a two-week date is foolish on your part. Both from a dating standpoint and a financial standpoint. You’re willing to spend thousands of dollars to hang out with someone because they flirted with you on Facebook? Here’s a better idea: Use that money to do fun things where you can meet women you can actually date and build a real connection with.
Seriously, this is a terrible idea and the answer remains: Nah. Continue to message her, build a connection, but work to build connections with people you can actually form adult relationships with, not pen pals who will only hang out with you if you pay to see them.
Good Luck Out There.