A
male
age
41-50,
anonymous
writes:This will seem funny for a 34 year old man to be seeking advice on. Basically, I go to the same shop a few times a week. There is a lady works there who has really caught my eye, whenever she is there when I go in, I get butterflies and feel all nervous and I’ve started thinking about her a lot. Problem is, I am so rusty at the whole dating thing as I have been single for a couple of years, so I have no idea the best way to go about asking her out. Do I just straight up ask her out when I bump into her? Send her a valentine with my number in it? What would the ladies of dear cupid prefer a guy to do if he liked you? Please help! Reply to this Question
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female
reader, anonymous, writes (3 February 2017): That is great news, OP!!!
Wishing you both well!!! :)
A
female
reader, anonymous, writes (3 February 2017): Delighted for you best of luck!!
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A
female
reader, Honeypie  + ♥, writes (3 February 2017):
 Good for seeing the opportunity and to "read" her information right.
Good luck, I hope it works out well for the two of you!
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A
female
reader, Andie's Thoughts +, writes (3 February 2017):
 It's good that you talked to her first, so it wasn't creepy or too unexpected. Good luck - 27 and 34 isn't too bad because you can still be at similar life stages.
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reader, anonymous, writes (3 February 2017): This is verified as being by the original poster of the questionUpdate on situation: So I've still being going to the shop (not to stalk her,I need milk and bread often. Haha) Anyway, I was in shop and couldn't find eggs. I went and asked her and she took me to them then she laughed and said even she gets confused as they so often move stuff. She then made an awful joke about eggs and apologised. I said I also love bad jokes. Anyway,we got into a conversation and Valentines day was brought up. She said "Sadly I won't be getting any valentines this year" so obviously she's single. So,I thought what the heck and just asked for her number. She gave me it,we have been texting a lot and we are meeting Saturday afternoon for coffee then going for a meal and a comedy show in the evening. Turns out she's younger than I thought at 27,I'm 34 but that's not an issue for either of us. I can't believe my luck, she's so so beautiful and is coming across as a very sweet and caring person with an awesome sense of humour (terrible egg jokes aside. Haha). We have agreed to take it slowly as both been badly hurt before.Thank you so much for all the answers. All very much appreciated that total strangers would take such time to help me.
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A
female
reader, anonymous, writes (3 February 2017): I agree with some of the others. Get to know her for awhile before you ask her out. Talk with her and be friendly. Feel her out. Find out more about her. You frequent the shop regularly so you do not want to do anything that could cause awkwardness in the future.
I would say be nice and casual. Do not linger too much. Talk to her in a way which progresses and build up to rapport with her. Baby steps.
You will know if a woman is interested in you by how she responds, what she says or doesn't say. How she looks at you etc. But also remember she is in her place of work and must be cordial to everyone. Therefore gauging a true reaction may be difficult.
You can ask her for coffee if indeed you are a risk taker. Nothing ventured, nothing gained. But be prepared for the negative outcome as well. If you are and are able to live with it, then you will be able to do it. If you are the type of a guy who cannot handle rejection well and would be mortified if she turned you down and would never want to show your face in the shop again, then do not take risks.
Some men are direct and forward and can handle if the woman says no. Others approach in a round about way in order to save face and their ego if rejected. Depends on the man himself. Which one are you?
If she rejected you, could you happily continue visiting the shop and being friendly to her as if nothing happened? Or would you banish yourself from the shop forever because you are embarrassed?
Women are usually flattered by male attention and displays of affection, as long as it is not creepy or obsessive. So always keep it light.
I think you just need to talk to her and find out what her situation is. It is hard to plan. You need to just start talking and go with the flow of the conversation. I find that usually when the conversation starts to flow, you will know which direction to lead her in. And you will know what to say. Never plan. Just go with the moment. I think the Valentine is too excessive for now. But a single rose might not be. Maybe a rose which signifies friendship as opposed to a red rose, which signifies love. But you will definitely be showing your interest with a rose!
I personally am a risk taker. I can live with the negative outcome. For me, I would rather know than live my life with regrets by never taking a chance. At the end of the day, at least you tried. And you can live with that.
I wish you well and hope she likes you back!
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A
female
reader, seg1 +, writes (30 January 2017):
 I wouldn't jump right into the deep end and ask her out right!
Every time you go in there make small talk ask her how her day is etc try find out if she is in a relationship or not? Have some banter with her and see how she reacts to it. You can tell a lot about a person's body language!
If its a case of she is single then why not send a valentines card or ask her out right? you've got nothing to lose!
Don't put yourself down! If you want something go out and make sure you get it. Think positive..Good luck!:)
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A
female
reader, anonymous, writes (30 January 2017): Well.... to begin with I would say just say 'hi' and see what response you get. You won't really know until you chat a little on at least acquaintance level.
I worked in a place where I met many people and not once in 3 years did any guy come up to even say 'hi' even though we were in the same areas many times.
I think it takes guts, but if you can and you do.. what do you have to lose?
Test the waters and see!
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A
female
reader, Honeypie + ♥, writes (30 January 2017):
I would NOT ask her out right off the bat. I would start with some small talk so you can learn her name and maybe if she is single.
If she is married or have a BF a Valentine and offer of a date might not be a great move, especially if you want to continue to use the store.
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A
female
reader, anonymous, writes (30 January 2017): I like a really forward guy. I had a man once jog past me (exercising) ... he did a u-turn and came back and said:
"This might be a bit weird, but I think you look beautiful so I thought, what the heck, I'd like to ask for your number." And he was really nervous - not at all full of himself!
I was taken aback, such a compliment - I thought fair play to him - and I told him if I was single, I would have taken his number. (He wasn't especially attractive, but he had courage and also a sense of modesty!)
So, that's my story - I like forward men, and I say go and do it! Also, and the next bit is really important - You might not regret the things that you do, but you will definitely regret the things you don't do!
PS: A valentine in my opinion is a bit too mushy (she'd either hate it or love it) so maybe minimise that risk and just straight out ask could you have her number or tell her you'd like to take her out for dinner!
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A
female
reader, Andie's Thoughts +, writes (30 January 2017):
How old is she? We've seen a couple of posts by men your age about women working as a cashier or waitress who they have a crush on without ever really speaking to them.
You like the way she looks and that's it. A Valentine's card would seem creepy, in my opinion, so I think it's a bad idea. It's also not a good idea to just ask her out without even striking up a conversation with her.
OP, if she looks to be your age, start a conversation with her. If you don't, you'll have no clue about her personality. She might have a voice you can't stand or talk in slang. She may be a lesbian or already married.
Asking people on a date when you have absolutely no idea about them is such an odd concept tonne - especially when she may get hit on a lot, when she's just there to work and isn't left alone.
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