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Pointers on Asking your friend out on a date?

Tagged as: Dating, Friends<< Previous question   Next question >>
Question - (22 April 2011) 5 Answers - (Newest, 22 April 2011)
A male United States age 36-40, *olidus writes:

I've decided on asking one of my female friends out on a date. Do you guys have any tips on how I should go about doing this? For instance, since we're already pretty good friends is it appropriate If I were to simply text her saying something like "Hey Rebecca, how would you feel about going out on a date with me this weekend?"

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A reader, anonymous, writes (22 April 2011):

"It's absolutely NO problem to get her to do stuff with me alone" problem solved then. Just invite to your place for dinner, candles, crack open a bottle of wine (or not), watch a movie and just get cozy. See where it goes from there. You can talk to her about feelings or you can see what happens.

Personally I don't like the 'feelings' talk, it's awkward for both people and it can ruin a night if feelings aren't reciprocated. I like the softly, softly approach. Easing her gently in that direction. Firstly inviting her to your place is immediately a more private intimate place than a public date. There are no distractions and you don't have an audience. If she's anti-PDA (public display of affection) then it will be easier to have more intimate conversations and/or flirting. You can make the atmosphere a bit romantic.

That would be my next step, I'd test comfort levels by flirting a bit, nothing over the top but I would see how comfortable she is with light touching on the shoulder in conversation, flirty talk etc. Basically just a little extra than usual and see how she responds. A bit of playful flirting is fine and you can gradually build on that until you eventually make a move by either talking about how much you like her or go in for the kiss if it feels right to do so.

Dude dates are kind of for girls you want to get to know, you already know this girl and have already been on friend dates with her. You can skip that whole process now and see if she would be open to start seeing you. Then of course you can arrange proper dates. But as far as asking her outright for a date there's no need, plus it kind of puts a bit of pressure on you both and it would be awkward seeing as you both would have already gone out quite a bit alone as friends. I do agree with mishmash in that her willingness to spend time with you is a good sign. So why not just ease her into dating instead of, all of a sudden, putting a label on it or asking her out. You're in a position where you don't have to do that.

You're in a position where you can just add romance to your normal dates and gradually get to the point where you can take it to the next level if she's up for that.

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A reader, anonymous, writes (22 April 2011):

If you already spend time with her alone...yes, I think you can use the word "date". Alternately, you might just tell her you have feelings for her.

If she goes out of her way or travels some distance to see you and spend time with you alone, I'd guess you probably have a good chance of success with her.

Good luck.

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A male reader, Solidus  United States +, writes (22 April 2011):

Solidus is verified as being by the original poster of the question

Solidus  agony auntThis is all very good advice, however I have a question concerning the wording...Cerberus says that I should make sure she KNOWS it's a date and mishmash says NOT to use the actual word DATE.

Which in lies my dilemma because I don't want to scare her off, but I also want her to know that this is a romantic date. I asked her out to sushi the other day at this low key little spot, and we went and had a great time, but I got the feeling that she probably thought we were just hanging out!

It's absolutely NO problem to get her to do stuff with me alone, but we live a little ways from each other so the only time see each other is when we make plans to hang out.

So how do I make it a date without saying date? I think "Would you like to see this show with me?" might be too subtle.

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A reader, anonymous, writes (22 April 2011):

Cerberus gave you pretty good advice. Ask in person, don't text her...she'll think you're a coward if you do.

Since you're already friends with her, you have some advantages:

-you likely know her interests and hopefully have some insight to what an ideal date would be for her.

- because she already knows you, she's far more likely to agree to it as well since she feels at ease around you.

I wouldn't phrase your question with the word "date" though. If she thinks of you strictly as a friend, she might react to the vocabulary and refuse outright. The magic words I've discovered are "with me"

For example:

Would you like to have a drink with me?

Would you like to see this show with me?

It makes it pretty clear you want to spend time with her alone.

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A reader, anonymous, writes (22 April 2011):

First off ask her in person. Texts are very impersonal, plus it can be horrifying waiting for response which can take hours because she'll probably want to consult her friends about it. If you're not going to see her any time soon then call her. Seriously don't text, waiting really sucks.

Have something planned, an idea of something to do. Cinema, drinks something like that. The best chance is if it is something you know she'd like. A gig or something like that. If you just ask her out without a plan then her next question if she says yes will be what will we do and you don't want be stuck without a plan in that situation. Have a few things in mind too, look up what's happening in your area so you have some alternative suggestions.

Most of all though approach this casually but confidently. Your attitude should be such that you have a really cool idea for having some fun and you thought she might like to join you. No big deal, but do make sure she realizes it's a date.

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