How to approach a crush? And does it change as you get older?

[TrainOfThoughts]

As I went out of a long-term relationship, I was struck with the painful realisation that I was, indeed, out of practice. Not quite sure how to approach a lady I'm very interested in - I think she's too. Nothing went beyond staring and smiling at each other.

In my early 20s, it was relatively easy and didn't think twice about approaching somebody or flirting with them. But now, being 37, I'm not sure what to expect from a 30-something-year-old lady. The 'girls' I went out with are now 'ladies', so to speak.

Does the 'approaching technique' change? Does women's receptivity to guys approaching them change as they get older? What do they expect? How to talk to them "out of the blue"? How not to come across weird or scare them off?

I'm aware my questions sound a bit naive, but you have to remember I was with the same person for 9 years and totally lost touch with the 'game.' It's like waking up to a whole new reality. The broken relationship made me, perhaps expectedly, more sensitive to rejection. Hence the questions.

Thank you!

Not quite sure how to approach a lady I'm very interested in - I think she's too. Nothing went beyond staring and smiling at each other.

What's the context you see her? Is this at your work but someone you don't know or is it total stranger on a train platform?

If it's someone you see regularly (like on the platform or on a way to work), just start with a smile and actually saying hello/hi as you pass but don't stop to talk or force a conversation. Keep at it until it becomes comfortable.

Then when you feel ready and the moment strikes you, just add in a comment - preferably with a question - that occurs to you and feels natural. It doesn't matter what it is - it's probably better that you don't pre-plan so it is natural. Do NOT make up a forced compliment unless; compliments only work if natural and meant.

God it's cold isn't it?
I love the colour of your coat it really suits you.
I read that book last year. I thought it was great/rubbish. Are you enjoying it?
We must stop meeting like this. Do you work near here?
It's ridiculous I see you every day and we never speak. Hi my names Train.

What you need to remember is that if someone is interested in you, it actually doesn't matter what you say (as long as its not offensive or insulting!! LOL) because talking is just a bridge to connect. If someone is receptive, any old crap about the weather will do.

Also what's the worst that can happen? Absolute worst is that she isn't interested because she's married/has a bf/is gay/not attracted to you. That's not so bad and doesn't really change where you are now.

Do you see her often? If so, just start talking to her. After a while, invite her for a coffee or a drink. If she likes you she'll agree.

I see her almost everyday on the way to work. Also, she lives nearby.

Oh, forgot to mention, I sent her flowers last week and signed it with my initials. Would it be OK to use the flowers as a conversation opener?

Did you send flowers to her home? I would find that a bit spooky, especially if I'd never spoken to you, slightly stalkerish. You've told her you know where she lives. Does she even know your name? I think you've actually made it harder for yourself now. If you approach her and use the flowers as a conversation opener, unless there's a reason for you to know where she lives, you risk coming across as a bit scary.

Just go up to her and say you've noticed her a lot, and would she like to go out for a drink.

As I've got older, I've got bolder. I asked my now DH out directly. What's the worst that can happen? She says "no thanks".

@Brakebackcyclebot No, not her house. I don't think it's stalkerish if I send the flowers to her mum's house who's actually my neighbour. Strangely, since I did that, her mum has been extra nice to me ...LOL. I think she probably knows. Yes, she does know my name. And since the flowers, she's been more noticeably more keen in the way she looks and smiles at me.

Ok, that sounds better!

Just ask her. You have nothing to lose.

Do I need to strike few conversations with her before asking her out? Or just walk up to her and do it?

Well if you've sent her flowers your past the point if subtlety! Ask her for a drink.

You've sent her flowers. Now get on with it! Ask her out for a drink.

@Cricrichan

Cool, I like straight shooting.

Thank you, guys! Will do it. Like you say, nothing to lose.

Just bloody do it!!!

So, today, she comes and stands a couple of feet away from me. I turn around with the intention to strike a conversation with her (she was looking at me and perhaps expecting me). Then, bang! Her friend...AGAIN...rushes in out of nowhere and blocks me. This time she actually dragged her away from me. The 2 feet turned into 20.Yesterday she just stood between us when I tried to walk to her. and today she basically took her away. What the hell is this? I really wanted to slap that friend.....feeling furious!!

Oh come on TrainofThoughts! Her friend being there makes it easier to start a chat. It's less full on if it's not one on one.

You are looking for excuses.

@PaperRockMissile

Not at all, I was literally walking up to her when she came between us. Was I supposed to jostle through?!! You see, I'm pissed off..not relieved. That tells you something.

Curious, how does her friend being there make it easy?!!

Sounds like her friend is on call to separate her from scary send-flowers-to-her-mother guy , which is btw beyond creepy and well into serial killer territory.

I'd sack this one off and get onto online dating if I were you, where women are guaranteed to be actually interested in meeting someone.

Curious, how does her friend being there make it easy?!!

???

Because it's always easier to engage two people in conversation than one if you are trying to chat one of them up. It's less confrontational and its more relaxed. Two people provide two different points of view and two different conversational strands and two people to fill silences.

Plus two people have no idea what the other one is thinking so are less likely to be rude/cut you dead because for all A knows you could be an old friend of B.

I'm surprised you had to ask why it's easier. Do you interact with humans much?

If you are shy it's easier to manage a group conversation.

And so what if she came betweeen you. I still don't buy the pissed off not relieved. It's not that hard to walk round the side and say "hi. I was just coming to say hello". Are you 12 years old?

However, I agree with NotTheFord though in the light of your last post. If it was a deliberate blocking move, it maybe the friend has been told all about it and deputed to "save her" from the creepy stalking man sending flowers to her mother (which I do agree was a bad idea. really bad idea. you'd have been better off walking up to her and giving her flowers to her face).

I'd forget about it for three reasons - one, it seems that there is a real prospect the friend was intervening deliberately - which suggests your target wants diverting assistance. two, if she knows you sent the flowers, it's a great excuse for her to say to you "thank you for the flowers." if she's interested - she hasn't. three, the best relationships are easy - if you actually can't manage to speak to her just because her friend walks up - there is too much angst around this for no gain.

Walk away before you get a harassment warning.

OK, I appreciate you're evaluating the situation based on what I said. But it's not as 'stalkerish' or as 'creepy' as you have pointed out. It's very difficult to paint a clear picture of the situation. By the way, people don't come and stand right next to their 'creepy stalkers' and stare and smile at them constantly :)

However, none of that matters now as the situation changed drastically since my last comment...

I saw her this morning and she was alone. Walked up to her and struck a conversation. She was very receptive and nice. I can't believe I began by talking about the weather, couldn't be more British, could I?! Plus, I hate the weather talks LOL. But... Guess what? I've got her number now and we're having a drink this weekend.

So, things worked out eventually. We'll see how it goes...

Thanks!

Oh,,that's lovely, and soon be Valentines day, some more flowers perhaps, and more steps in the right direction.

Walked up to her and struck a conversation.
Hoo- bloody-ray!

See it wasn't difficult. All this angst over a simple chat about the weather.

I've got her number now and we're having a drink this weekend.

About time. Good luck OP.

@PaperRockmissile

I know, right?!

I guess I was a bit nervous to begin with, but when she smiled and seemed receptive, all the angst just disappeared.