Should I ask this girl to a date this summer?

March 31, 2012 9:01 PM

Should I ask this girl to a date this summer? If so, how should I ask?

Hi all!

(The song I'm listening to while writing this post: http://www.youtube.com/watch?v=QrojFR7jM9E&feature=relmfu)

This girl and I have went to the same middle school and high school together. During our high school, we went through a highly selective program with less than 50 people in our program, and everyone had the same classes for four years. So we know each other very well. However, we are not close friends. So I should say, we know each other's personality very well.

She's a good girl, never uses profanity, texts with perfect grammar, has a lot of friends but is usually quiet, and has a good temper. She had only one boyfriend before.

She had helped me before when I wasn't doing well with another girl in this high school program (I've never had a girlfriend before). She described me as "You are extremely smart, nice, funny, and talented." We got close in those couple weeks, but then we drifted apart again as we are now in college. I still text her once every one or two months.

The problem is that she has gone to a college four hours away, while I stayed.


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My first question is.... is it worth the effort?

I think it's worth it. Since we are old friends, we already have warm feelings toward each other and know each other very well (When she was comforting me after my failure with the other girl, she said "You are an awesome guy and any girl will be lucky to have you in her life.")

On the other hand, since we have already drifted apart some, even if she rejects me, I wouldn't risk losing too much of a friend.

What do you guys think?

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I'd like to ask her to a date (and possibly more than one) this summer as she comes back to our hometown. I'm thinking of planning a camping trip reunion for our small high school program. At the end of the program, as she leaves, I would ask her if she wants to go to an ice cream shop with me sometime. I've been arguing with myself how to form the question. Some guides out there say to use the word "date" in the question and make it clear and obvious of my intention so that she wouldn't think it's just hanging out. Some say to make it casual and not use the word so that it wouldn't be too much pressure on the girl.

I'm more leaning towards the second option. However, since we are old friends, such an indirect way of asking her might make it seem like we are just hanging out. Nevertheless, I do think asking her face to face would make it more obvious.

So I guess my second question is how I should word it?

Thanks everyone for your input!

— Thisispiggy

posted by Thisispiggy to human relations (14 answers total)

"It's great getting to spend time with you again, want to go on a date with me? We could go to the ice cream shop!"


The word "date" will feel awkward as you are saying it, but you are taking that in exchange for weeks (if not MONTHS) of dancing around the "are we dating or are we just good friends ahhhh soo difficult" debacle. Good luck! This sounds promising!
posted by estlin at 9:06 PM on March 31, 2012 [1 favorite]

Hoo boy you are overthinking this. Yes, you should ask her, you just need to go for it, and if you say "Can I take you out for ice cream/dinner/to the movies sometime" you'll send the message it's a date.
posted by schroedinger at 9:20 PM on March 31, 2012 [11 favorites]

I think asking her out on a date is a good idea, though I'm wondering if there's a way for you to do it without the camping trip. First of all, in case she decides not to go*, and second of all, because you may be competing for her attention if there are other guys from your program around, and you think that being a guy from her program works to your advantage.

I will say that I hope you're open to something popping up with someone else in the mean time. Summer's a ways off, and if you're thinking things through this far in advance, you may be more invested in this than it would be healthy to be.

(*You may have more info on her interest in the camping trip at this point than I'm able to get from your question.)
posted by alphanerd at 9:21 PM on March 31, 2012

Aww. This is so sweet. I think you should just ask her on a date, with the word "date," because she sounds like she's cool and that way you'll be upfront with her. As you say, if she says no, the stakes aren't too high. Good luck!
posted by stoneandstar at 9:25 PM on March 31, 2012

My wife and I are in agreement - if a girl is willing to go on a date with you, whether or not the exact phrase you use contains the word "date" will not affect her answer.
posted by tylerkaraszewski at 9:45 PM on March 31, 2012 [1 favorite]

Unless you're coworkers, or one of you is the other's boss, or one of you is in a relationship, the answer to "should I ask her out" is always yes.

Why is that? This is why.
posted by Ragged Richard at 10:28 PM on March 31, 2012 [7 favorites]

" if a girl is willing to go on a date with you, whether or not the exact phrase you use contains the word "date" will not affect her answer"

That's not really the point though - the point is, if he says "wanna get some ice cream" and he thinks it's a date and she thinks she's just getting some ice cream with her old high school friend, then he's no closer to an answer and she's been put into what will eventually become a really awkward situation.

OP, I think you should ask her out, making clear that you are interested in her as more than a friend, whether or not you use the word "date." But I also think you need to chill out a bit. Summer's not for several months - she could be dating someone else by then. (I might have missed it, but are you sure she's not dating someone else now?)
posted by DestinationUnknown at 5:12 AM on April 1, 2012 [3 favorites]

Ask her to do something specific with you: activity, date, time, etc.
posted by Carol Anne at 6:22 AM on April 1, 2012

Thanks for all the response! I like schroedinger's idea of using "take out." That makes the intention clear without being too awkward :)

Perhaps why I ask so early is because of two reasons:

1. Summer for us starts in a month, and I have to start planning the camping trip (making reservations, sending out invitations)

2. If this were successful, this would have been my first real date with anyone. So it's kind of nerve racking haha.

I'm pretty sure she's not dating someone else. And if she is, that's ok too. I've learned from my last failure that there are plenty of fish in the sea.

Also, if she does not come to the camping trip, would it be better for me to text her for a hangout somewhere first and then ask for a date then?
posted by Thisispiggy at 9:15 AM on April 1, 2012

You know, this might sound weird but you've got at least a few weeks at your old school left. Why not go on a few dates there as well? (sorry if my assumption that you aren't is wrong.) You will have a chance to work out some of the nervousness and have a good time before this summer.
posted by dawkins_7 at 9:16 AM on April 1, 2012

Old school? I'm a freshman in college.

And it's because I've never been on a date before, well, except for Prom.
posted by Thisispiggy at 9:18 AM on April 1, 2012

... This girl and I have went to the same middle school and high school together ...
... She's a good girl, never uses profanity ...

Skip this one, you need someone from outside the hothouse. Go get lost and into trouble.
posted by ead at 10:22 AM on April 1, 2012 [1 favorite]

" if a girl is willing to go on a date with you, whether or not the exact phrase you use contains the word "date" will not affect her answer"

However, if a girl is NOT willing to go on a date with you, whether or not you use the word "date" will affect her answer.

The key is that the point of asking someone out is not to get them to go out with you -- it's to find out if they want to go out with you. A "yes" is more desirable than a "no", but both are preferable to limbo. Endless, soul-sucking limbo.
posted by endless_forms at 12:04 PM on April 1, 2012 [1 favorite]

Yes, ask her out. Use the word "date" and smile when you do so. Keep it simple - don't apologise or give her an explicit reason to say no in the way you phrase the question. It will most likely not be awkward when you ask, unless you make it so.
posted by hootenatty at 6:16 PM on April 2, 2012 [1 favorite]