John asked: “This girl has come into my life and she’s very damaged from past relationships. I’m not as much seeking damaged women to help them, I just really like this girl and want to help her. She doesn’t trust me, right, which why would she because she doesn’t know me that well. We have been spending a lot of time together. I think she’s just really scared of getting hurt again, and I don’t really know what to do, but we had so many past experiences (even damaging ones) that are identical. She seems to not be overly into me and partly needs a friend right now, as do I, however at one point she jokingly said she’d go out with me for ice cream if I had sideburns and died them magenta. So I got fake sideburns painted them and took her to ice cream she seems very happy and flattered then she just got very distant. Any advice?”
Liz says: I’m going to put it out there right off the bat that magenta sideburns as a date requirement is ridiculous. Clearly the facial hair was not truly mandatory for her to be into you, since you obliged her request (albeit by faking it) and then she got distant. My guess is that she joked she’d go out with you if you got the dyed sideburns because she thought you wouldn’t grow them, as if to say “I’ll go out with you when pigs fly/when you become a millionaire/when you have magenta sideburns.” On one hand, it’s endearing and funny that you showed up with a false set, on the other, she may have perceived it as a sign of desperation or weakness.
And why is going out for “ice cream” the date of choice? Not that there’s anything wrong with getting frozen dairy desserts together, it just seems an oddly particular choice. I have my own personal love affair with Ben & Jerry, but I don’t think I’d ever hint to a guy that I’d let him take me out to the ice cream shop, like it’s 1952. It’s possible that she was using an ice cream shop the way some people use a coffee shop, as a friendly (read: lower-tier) date.
Anyway, you mention that you two have been “spending a lot of time together”, but then say you understand why she doesn’t trust you “because she doesn’t know me that well”. It sounds to me like you both know each other pretty well, since you’ve both disclosed personal stories to each other in intimacy that lead you to assert you have so much in common with her. While it’s understandable that someone might build walls around themselves after dealing with past rejections, this seems more like she’s simply enjoying your friendship more and may not want to be your girlfriend, which you’re obviously aware of because you stated “she seems to not be overly into me”.
This means you either have to accept she probably wants to keep things platonic and maintain a friendship, or decide if you’d rather be her boyfriend and will move on if she doesn’t want to be your girl. The quickest way to decide which road to walk down? Ask her out on a real date! Tell her how you feel about her and tell her you’re going to take her to dinner. Her response will tell you what to do.
If she accepts the dinner date, make sure you dress nicely for it, upgrading the wardrobe you usually sport when you two hang out as friends. Present yourself as someone who is ready to slip out of the Friend Zone. And for the love of Romance, don’t take her to some hole-in-the-wall dump. Take her to someplace that’s a step up from wherever you two have eaten before. If she stalls on going out with you, and isn’t clear about her feelings, then you know she’s probably trying not to hurt you by being honest. Don’t be that guy who keeps lying to himself about how she just needs time to trust you, and don’t waste time believing that you can “help her”. A girlfriend shouldn’t be a self-help project. That’s what therapists are for.