I'm in a somewhat weird situation.

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Ok. So I've been trying to ask a girl named Michaela to be by my side. I was at a party tonight because it was my friend Rebecca's friend Hinano's birthday (she's a foreign exchange student from Japan). Sarah is my Ultra-Mega best friend who also happens to be my very first High School crush. Sarah was also at Hinano's party. I've been going to Sarah for advice on what to say to Michaela. I actually consider Sarah to not only be my best friend, but my Wingman. Last week, Sarah messaged me while I was watching Grease Live. We are big Grease Fans, so we spent the whole time criticizing how bad we thought it was. Sarah never clarified her reason for messaging. So tonight at the party, I asked her why she messaged me, and she told me to text her later, so I did. She asked me to go with her to prom. I asked my mom what to do and she told me to ask for the details and I did. She also told me to say yes. I managed to tell Sarah that she was my first High School Crush, and she told me that she was currently crushing on me. I just don't know what to do with all of this anxiety. I also don't know what to do about Michaela, but I never got around to asking her to be mine. AND COINCIDENTLY, ALL THIS IS HAPPENING RIGHT BEFORE V-DAY.

Its not really weird its just uncommon for guys like us lol.

As a rule i would not date my best female friend, because if things go bad chances are she wont be your friend again. Nothings set in stone yet, your still single. First thing i would do is find out if Michaela is into you. If you've pretty straight up told Michaela you like her or someone did and she hasn't shown interest there's a good bet shes not keen. Trust me dont pursue this lol, wont work out. But if you dont know bro well you gotta find out.

Women can be really hard to work out, even for neurotypical guys lol.

Yeah i get the V-Day bit, welcome to my world sucks being 30 something just another big consumer day for retailers.

The first day I met Michaela, she held my hand. I thought she was just some overly-friendly person.we eventually been sitting with each other almost every day at lunch, and she eventually embedded herself into my main group of friends. I think I've always been attracted to her, but I didn't know how she felt. One day she straight up told me she loved me. I wasn't sure if she meant as friends or if it was a joke or something, but I sort of pretended like I didn't hear it and tried to move on from it (I probably shouldn't have done this). it was the week of V-day 2014 and I went to the V-day dance with another girl named Haley. WORST NIGHT OF MY LIFE, AND MOST LIKELY THE SAME FOR HER. there was so much anxiety and Ghetto Booty-Grinding music and then I pretty much shut down. I also thought that things would be salvageable between Haley and I. Nah. I then began to get even more and more attracted to Michaela after that. one time we were talking among our group of friends and she told me she didn't love me because I was the same age as her brother.....

She was 17 and I was 14. I began to wonder if she had really meant what she said, or if she was afraid of getting hurt or something...

I don't get why her reason was that I was the same age as her brother. One time, she told me what kind of panties she wears, which I'm pretty sure she wouldn't tell her brother... . Another day, she kept calling herself Michaela (my last name) as if we were married or something... Another time, she was singing Disney songs with me and then told me that who ever she marries, will have to love Disney.


With all of these occurences, you can sort of tell why I'm confused about whether or not she was telling me the truth or if she was just trying to keep herself from getting hurt or something.....

Player.

But in all seriousness, you're doing very good with girls right now and from a fellow male about your age, I commend you for your success!

Firstly, I've got a few questions:

1. How likely are you to give Sarah a chance for a relationship? 1 being very unlikely, she's only my friend. 10 being 'I want her RIGHT NOW'.

2. Just how strong is your attraction for Michaela? Out of 10, one being 'quite low', 10 being 'strong, obsession'?

3. Do you think Michaela is aware of your feelings at all? 1 being 'not at all likely', 10 being 'she definitely knows'.

Now, here's what I suggest:

You don't sound like you have very much time at all to decide. Two people can go to a prom as just friends, but considering Sarah's feelings, she'd be very hurt possibly.

Alright, if the answer to question 1 is 5 or above, and the answer to question 2 is 5 or less, and the answer to question 3 is 3 or less, I suggest confessing your feelings to Michaela, and see what she says about it. You may risk getting hurt, but if you are rejected, you can immediately go to Sarah and give her a chance.

I don't mean to sound immoral, or that you're using Sarah as a 'back-up' girl, it's just your amount of time is extremely short here and tbh this is just my opinion but if you truly would give Sarah a chance, you're putting that on the line by attempting to pursue Michaela.

Thing is, you've got a near limitless amount of time to pursue Michaela, but it's not guaranteed.

On the other hand, you've got a short time-frame to pursue Sarah, and it's guaranteed she likes you.

You obviously cannot choose one or the other, so my suggestion is to, let's say, see which one you have a better chance of happiness with, and then going for them.

The fact you'e unaware if Michaela likes you or not, in my humble opinion, is a lack of information that is key to what your choice would be.

If you knew Michaela liked you, you would be able to pursue her and end up with her, and as unfortunate as it may be, have to let Sarah down gently.

If Michaela turns out to not like you, as much as you are attracted to Michaela, if you are even slightly interested in giving Sarah a chance, than just go for her.

I did something similar to get my second ex-girlfriend. I had been admiring her from afar a long time, a friend of one of my friends, but I was focusing on other girls at the time.

I was getting to know this one girl, but she rejected me and only saw me as a friend.

I decided to be bold and quick, and even if I barely knew the other girl, I quickly asked her out and we hit it off instantly on the first date, even if I never really spoke to her before.

She was my longest relationship at about 1 month and 1 week before she broke up with me.

It's not a rebound. A rebound is quickly beginning a new relationship after an old one ended. What I did, and what I suggest you do, is to look at all your options quickly and pursue the best one.

I also had very little time left: it was the very last week of the school year, and I was a high school senior, she a junior. Even if i asked her out, because of conflictting schedules it took us until the second last day of the school year before I could give her my contact details. Cut it pretty damn close...*phew*.

If what i say to you does sound morally wrong, like others have thought, than you have every right not to carry it out. Just trying to help so you don't end up with neither, something I've definitely experienced before.

I'd go out with your best friend. I can tell that's probably what you want to do because you only mentioned the other (who's Michaela?) chick like once in your whole first post. I'd love to date a guy best friend. Gotta get one first I suppose.

Plus you said your best friend already asked you to prom, if you say no it could also mess up that friendship. She's definitely going to be hurt.

When is prom?
Here, it is usually in May so that is a ways away. A lot can happen in-between. Can you tell Sarah (if you haven't already said you would go with her) that you will giver her answer at the beginning of April? This would allow for a no if something happens with Michaela in the meantime and would give her plenty of time to find another date. If nothing happens with Michaela, then the beginning of April would give you both plenty of time to get all the details together for prom. A couple of months in the world of teenage romance should be plenty of time to know if something is going to happen with Michaela or not.

OK...

Now for the actual girl advice. Michaela sounds a bit kooky to me. Holding your hand the first time you met? To outright say she loves you when you two aren't even in a relationship and haven't known each other that long? Then to turn around and say she doesn't love you because you are her brother's age? Telling you what kind of panties she wears??? This is just not normal behavior. This is *extremely* forward for a teen girl (I was forward, and nowhere near this much.) She sounds more like a girl who is emotionally needy and may have some serious issues. She may be going after you because you are available.

What I would do is ask Sarah what she thinks of Michaela, but DON'T HINT THAT YOU LIKE MICHAELA. This would only make Sarah feel bad since Sarah already admitted to crushing on you. Instead, say something like, "Michaela did such-and-such. Why do you think she did that?"

Unlike previous posters, I *DO* think it is a good idea (a very good one) to date best friends. I married my best friend. And if my best friend back in high school hadn't want to grow up to become a priest, we probably would have dated and ended up married.

The thing about best friends is that you have already learned how to work out conflict. You already know you like each others' company and share enough interests to do things together. A best friend isn't a best friend without getting through some disagreements here and there. Becoming a romantic couple doesn't change all that just because you've kissed or something. Best guy/girl friends have already been on "dates." The only thing you want to do is stay away from a sexual relationship, especially as teenagers. THAT is what causes problems. The ramifications of a sexual relationship can be serious, so you want to wait until you are older before dealing with that. It can destroy a relationship just because you're not ready to handle the possible consequences.

@nerdygirl:

In my experience that keeps happening to people around me I know, to MY disadvantage.

I had a crush on one girl, went on three dates with her, she rejected me because she thought she was a lesbian, changed her mind and decided she was bisexual, but not interested in dating ANYONE at the time, but was 'absolutely mortified' that she soon afterwards developed feelings for her best male friend. Since June, they are still together today, and in less than three months of their relationship, around, he proposed to her and they are now engaged.

My first girlfriend, just two or three days after the second time she broke up with me, started dating her best male friend that she's known for years and years. One of her main reasons was that she 'trusted him' more because I only entered my relationship with her as an acquaintance beforehand.

This one girl that use to have a crush on me, and I had a crush on her at the same time, was forced to leave school and drop-out due to family issues, and leave town and move halfway across the country. I started talking to her again after confessing my feelings but she only wanted to be friends. She has since stopped chatting to me online, and recently entered a relationship with her male best friend.

This other girl I had a crush on at school for a very short time, she thought she was ASEXUAL, yet in the end did end up heterosexual and with a male best friend. There was another guy who had a crush on her, and was rejected because she was asexual. I didn't even try and pursue the girl because I knew she was asexual and all of her friends did say she was, including a girl I was good friends with who I knew I could trust. You bet your life me and the other rejected guy complained about it together, but he was more accepting of the situation than I saw.

Looks like being 'just friends first' IS the right way to do things, but this upsets me because not everyone wants to have to do it that way, some of us just want to date and get to know someone a little than agree to a relationship. Is that too much to ask? Because both times I did it, I ended up with two very short relationships that didn't last long at all, and the first one was emotionally abusive and all give and no take from me and an unhealthy relationship.

SO YEAH. GO FOR SARAH OP. This is actually what I also secretly believe, but from what I read in your posts, I thought you are more attracted to Michaela.

i married my best friend. i think it's a wonderful basis for a relationship.