A
female
age
36-40,
anonymous
writes:I have never been good at flirting, first of all, but recently I don't know what has come over me with this new guy I know...It started with me and another girl getting him to promise to buy us ice cream because the weather was so hot. Then, a little later I brought a co-worker to the restaurant he works at and she said he was cute. Later, I told him through text she'd said so, and then I said "for the record, you are indeed attractive. But it might take five or more ice creams to get me to admit to that out loud." He joked around with me about that and then later in the week our friends (including the other girl he promised ice cream) started chatting about meeting up this Saturday for brunch... and him buying us ice cream, which the other girl included. I sent him a private text, asking if he planned to buy everyone ice cream. He said no, meanwhile everyone's demanding he buy them ice cream in the other chat.This is where insanity truly hit, because I said their ice creams could count towards me saying he's attractive out loud. He didn't reply after that. Not to the group chat or to me. So, we'll see what happens on Saturday. But, I wanted to get another eye on this situation because I feel like I stepped a little too far with this... Am I doing it wrong?
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female
reader, Honeypie + ♥, writes (25 July 2014):
 I'd quit with the free ice cream thing. My guess he he thinks that is why you flirt, to GET something FREE from him. And that is not exactly a compliment.
It might have been cute the first or second time, but you keep going on and on and on...
Now, I'm SURE he knows YOU and your friends think he is good looking. So If YOU want to get to know him, find another way that doesn't involve him "having" to gift you stuff to get to know him.
I've had people come up when I was a bartender, trying to charm me into giving them free drinks. It just felt dishonest.
So in that sense... I do think you are flirting "wrong" but flirting is not something everyone does well, it takes practise.
And.. if he is interested he has your number, doesn't he? Since you texted him several times already.
A
female
reader, llifton +, writes (25 July 2014):
 No, you're not flirting wrong. That's a pretty basic way of being flirtatious. However, it seems he's possibly not interested based in the fact that he didn't respond.
I think that you've made it pretty obvious you think he's attractive, and by ignoring your last comment, he was letting you know that he doesn't wish to lead you on or facilitate your attraction.
I would probably back off a bit and just lay low. See how things go. But I would hold off on this telling him you think he's attractive in person thing for a while. No matter how many ice creams are bought. He may not be feeling it. Just relax and be his friend for a bit. Then feel it out and see if you think he likes you.
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A
female
reader, confusedcupid  +, writes (24 July 2014):
 Flirting is supposed to be using body language to show your interested and small compliments and teasing. Saying he is attractive out loud is a step too far. Little signs are always best. Just wait for him to make a move on you.
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A
female
reader, Staceily +, writes (24 July 2014):
 I think it depends on the person. He may be a terrible flirt. He may not have been able to pick up on you flirting. He may just not be interested. I don't think you did anything wrong in what you said. You were playing around and it isn't a big deal. If he doesn't reciprocate or flirt back then okay, don't over analyze what you've said. Make light of it and have an "oh well" attitude. Maybe on Saturday say something to the effect of " so I was trying to flirt with you the other day but you were having none of that ". Laugh it off, poke fun, joke around. It shows confidence, like his lack of response didn't have you down or on dearcupid asking about it ;) Just be yourself. If this is the way you flirt then that's you, if he doesn't like it then talk to someone else. I think flirting is a lot about fun so don't over think what you say.
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A
female
reader, janniepeg  +, writes (24 July 2014):
 You might fancy him, but he probably sees it as getting free food, being embarrassed in the crowd, more than you having an interest in him. You would be putting him on the spot. Although guys want the world to know they are attractive, it's not something he's willing to pay five ice creams to be told that. It's fine if you are just teasing him and you want a good time with your friends, but if your intention is dating him then you are doing it wrong because I think guys usually want it to be a private matter. You would be putting him on a spot and giving him pressure in front of people.
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