I became friends with a girl named Penny around a year ago when she started dating my good friend Kyle; Penny and I became friends when she became a part of the friend group Kyle and I were a part of.
Over the past three months or so, Penny and I have been chatting a lot with each of us being each other's #1 best friends on Snapchat for the past few weeks. We often talk about each other's friends and relationships and vent to each other about stuff going on in our lives... plus a little "healthy" gossip.
We've also been hanging out more and more. Recently, Penny and I attended a weekend long event together in which we shared a hotel room and spent most of the weekend together.
Around three months ago is when I started to develop romantic feelings for her.
Around two months ago, Penny and Kyle broke up on relatively good terms. It's something she had talked to me about before it happened and she's talked about it with me a few times afterwards. Since then, she's been using online dating apps like Tinder with very little success as she is particularly used to dating people she was already friends with. I would also like to add that although I cannot be certain; I feel relatively confident that our friendship was not a significant factor in their breakup.
Honestly, my experience with relationships is very limited, only having dated one girl for three months in a very atypical situation. I have no idea whether or not she feels the same towards me as I've never (at least to my knowledge) have had a girl be particularly interested in me so if there were any signs that she was interested in me romantically or not, I wouldn't know.
I also suspect she is the kind of person who, based on her personality, would be "weirded" out if someone had romantic feelings toward her that she did not share.
Personally, this makes things feel kind of awkward for me because I feel almost dishonest not sharing this with her but at the same time, I'm sure both of us enjoy our friendship and I wouldn't want to mess that up. It's also weird since we talk about our dating "attempts" with each other (mostly Tinder mishaps).
- A good friendship with consistent communication and time spent together
- Her being the ex of a good friend of mine
- Little to no indication of whether or not she's interested in a romantic relationship
- The reasonable risk that asking her out might "weird" her out if the feeling isn't mutual
- I feel somewhat dishonest not sharing these feelings
How can I ask her out in a way that minimizes the risk of making our friendship weird?
I understand that if I'm rejected that it will mostly likely makes things a bit weird, but I'm looking for a way to ask her out in a way that seems less serious/harmless so it can be brushed off or a way that implies that if she wasn't interested, that I'd be "more than okay" just remaining friends and coping with my own feelings.
1.) As for the situation with Kyle, I'm firm on moving forward with asking Penny out regardless of his opinion on the matter. So although it may be a factor in how I ask Penny out, the question of whether or not I should ask her out BECAUSE of Kyle is not in scope. I will most likely be asking another question regarding how to tactfully deal with Kyle once I figure out whether I'm going to try to ask for permission (talking to him before asking Penny out) or forgiveness (talking to him after asking Penny out).
2.) Around the time we started talking/my feelings began to blossom into romantic feelings, Penny had discussed getting an apartment with me, although she seemed to indicate it was more of a financial/"finally moving out" kind of thing. It ended up not working out due to some financial issues on her end.
And if there is any more information I can give about our relationship, please ask. I tried to add all the details that are relevant, but since I'm rather inexperienced with romantic relationships, I'm not aware of a lot of the subtle things that could make a difference.