How do I tactfully ask a close friend out?

Question

Context

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).

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Question

Given:

• 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.

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Additional Clarifications

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.

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^{_{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.}}

Answer 1

There's no guarantee that things won't be awkward.

Most of the awkwardness after asking someone out comes from a re-contextualization of your relationship.

By asking someone out you will cause your relationship to be reexamined. Were you were only friends with them because you were trying to get with them? Will you treat future social engagements as between friends or as a potential date?

You can reduce the recontextualization of your relationship by framing it as a query between friends. If you asked a friend to hang and they said "no" the ask and the rejection wouldn't be a big deal. If you keep your request lightweight and friendly instead of dumping a big pile of emotions on someone without warning there's less about your relationship that needs to be reexamined.

Be clear and unambiguous. Give them space to reject you. let them know that you're cool with them saying no. Be sure that your actions back up your words if you are rejected.

If they don't want to go on a date with you it's imperative that you handle the rejection well. Acknowledge that you may have made things awkward, express a hope that your actions haven't complicated your friendship and try not to dwell on it.

Try saying something like:

I really enjoy hanging out with you. Would you like to go on a date? If not that's cool.

This expresses that you value their friendship, that you want to date them, and gives them permission to reject your advance if they don't want to date you.

Don't say something like:

I have strong feelings towards you.

This isn't something friends do. It's dumping your problem onto your friend. There's no way to reject the advance that isn't awkward. You're effectively saying "I have a problem, now deal with it."

Answer 2

How can I ask her out in a way that minimizes the risk of making our friendship weird?

Contrary to popular belief, you can ask her out and still remain good friends if she rejects you. This is simply due to the fact that what destroys the friendship isn't asking her out, but rather making a fool of yourself when she rejects you. This worst-case scenario would unfold like so:

You wait for too long and catch way too much feelings. When you ask her out, you're totally lovesick. You arrange a beautifully romantic date in a secluded spot, with rose bushes and everything, perhaps you extend a trembling hand and offer a wad of love poems you wrote for her, and then you're overcome by your feelings and you become a bumbling fool, and you move in for the kiss...

In the movies, she kisses you back with violins and everything. In real life, maybe she does if she's interested. However, if she's not interested and "doesn't see you like that" then...

• The "beautifully romantic date in a secluded spot" is a tricky situation to get out of.
• Your investment puts high pressure on her. You created a situation where rejection is difficult, awkward and costly for her.
• If you drove her there, then you will have to endure all the drive back in total awkward mode.
• If you start crying (because you're too lovesick, remember) and she consoles you, she will consume the entire energy of the friendship in doing so, after which it will no longer exist.

We haven't hit rock bottom yet. This would be when, the next day, you get drunk, and then a wonderful idea hits you: you're going to ask her out again! Maybe it'll work this time. You start with a long apology, then follow her in the street as she walks away, and then you insist, and then... oh yes...

Your excessive feelings increase the likelihood that you will say the Stuff That Should Never Be Said, like "But I was so nice to you!!! Why do you reject me!!!" which is the totally nuclear option, there is so much wrong in this sentence, she will treat you like radioactive waste for the rest of your life.

Then, of course, the following week you learn than she's dating Chad from the football team, and you conclude that Chicks Dig Jerks, and that women are evil for not wanting to date you, such a... a... such a NICE GUY! In other words you cast upon yourself the cringy curse of the Nice Guy. You die alone, bitter, and a virgin, but at least the fedora looks good.

Another option is:

• Rid yourself of the fear of rejection, as it is what will cause you to create the worst case scenario above.
• Do not fear awkwardness.
• What you will say when you attempt to initiate the relationship (ie, ask her out) does not determine if she is attracted to you. Either she is already attracted to you because of looks, personality, and past behavior, or she is not. Asking her out doesn't need some magic formula or anything. Either there is attraction or there isn't. Asking her out badly can ruin it, but it can't create attraction.
• Considering your current friendship, pick a low-pressure setting: you're both swiping through your favorite meat market app and showing each other matches and giggling.
• At the appropriate point, just mention "hey, why don't we date each other instead of doing this?"
• She says yes: you score.
• She stays silent and gives you the googly-eyed stare: wait five seconds and laugh it off. If you're lucky, she was actually interested and now asks you out. If you're a daring fellow, you can pile up the negs: "What? I've seen you without makeup, on PMS, when you're drunk, and you haven't scared me off yet..." This makes it easier for her to reject you if she wants by being crass on purpose. You're not pressuring her, remember. It conveys that you're not being truly serious, thus she won't feel like the friendship is at stake because you'd be angry if she said no. Also it's true.
• She says no: you laugh it off and go back to browsing. No drama. Not fearing rejection means you don't get butthurt or whiny, and you do not exhibit Nice Guy symptoms. In fact, you exhibit your cellphone, and suggest a threesome with the girl in the picture. Everyone laughs, case closed.
• And then maybe she thinks about it for a day or two and then she asks you out.

Just compare the two scenarii. And remember, in the first one, I was too lazy to write about when she calls the cops, but it's in there somewhere.

sphennings makes this interesting comment: "Ask yourself why things are awkward after a friend is asked out? Saying "I have feelings" is dumping a problem onto a friend and imposing on the friendship. It has an unspoken "I want you to do something about it." tacked onto the end."

This is my worst case scenario. In the way I propose you do it, you don't do that, instead you suggest you're a good match for each other. Don't mention you have feelings.

Answer 3

What things come down to is that you have a good relationship with this girl, and have feelings for her. She may or may not share them, although the fact that you get along so well may be an indication that she does.

Your question (How can I ask her out in a way that minimizes the risk of making our friendship weird?) is difficult (if not impossible) to answer without being very familiar with your relationship, and your communication style.

However, what things really come down to is that you're in limbo. You stand to lose her friendship if she rejects you, but it's also difficult to live with this secret crush weighing you down.

There's no great way to minimize damage to the relationship when you ask her out. The important thing is that you go though with it in a respectful manner, which does not pressure her to give a particular answer, leaves her the opportunity to gracefully reject you, as well as leaving no ambiguity between you guys.

You guys seem to chat/meet up often enough. There's going to be ample opportunity for you to try and ask her out. I would advise being fairly forward about it. Make your feelings clear, and see how she reacts.

Asking her out in a covert manner, leaves the door open to her misinterpreting your request, and leading to unpleasant complications. Being honest ("I have feelings for you") is better than muddying the waters to no clear outcome ("I want to hang out together more"). There's lots of ways to do this, and you'll have to find a way to express this in a manner that makes sense for you / your situation.

Don't do something like this: I was once part of a group of friends who conspired to create a 1v1 situation between myself and a girl whom I suspected had a crush on me, but I was decidedly not interested in. Imagine my surprise when I show up at the agreed meeting spot, and texts start coming in announcing that all these other people suddenly can't make it. The girl still showed up, and we had a pretty good time. However, an awkward moment came at the end where she thought we'd just had this great date, and expected a kiss. I decidedly ignored her hints, which lead to her not speaking to me for a good, long while. You want to avoid any such situations, and be clear as to your intentions.

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As far as Kyle is concerned: him being on good terms with Penny regarding their break-up does not mean that he'll be on good terms with you for making a move on her. He'll know that you guys were talking prior to them breaking up, and he'll undoubtedly wonder how much of a role your conversations played in their breaking up.