Coworker (let's call her Anne) and I started talking a lot and hanging out almost every weekend after her fiance dumped her. Thought she might be interested since she told me a lot about her personal life and text me random stuff often.. Anne also showed many signs of friendzoning: talking about guys she found attractive, asking me to hook her up with my friends, saying "I dont date younger guys" in front of me (I am a few years younger than her), and also tried to hook me up with one of her ugly friends (whom is her best friend).

3 months after we started talking, I flat out told her I liked her. She felt a bit awkward when I dropped the news, but we still talked for about 2 weeks as if nothing happened. Then she goes cold on me. It took me a few weeks to realize she wants space.. which I did give. After 3 months of going cold, she hits me up again. It took me a few days to decide if I wanted to see again.. which I decided yes. I was totally prepared to never hear from her again.

We've hung out a few times since we reconnected. She's paid for dinner every time.. but I always drive. She's currently seeing another guy, but went as far to say "who knows, next time I see him, I may find him uncompatible".

I tried throwing out some signs of interest to see how she reacts, but no positive response. Such as...
Her: "What if I never find a man?"
Me: You got one right here (referring to me)
Her: Hahaha you're stupid..

3 weeks ago, I smooched her on the cheek as I dropped her off at her house after a party. She didnt kiss back or pull away, but also didnt show signs of discomfort. That smooch was my sign of "Im still interested", and my plan was to not contact until she initiates. She never initiated, so yesterday I hit her up to hang out in 2 weeks and she said ok.

When Anne and I hang out, it's always just us 2 and I can usually get her to come out. What's different this time than before I told her I liked her is that we don't text everyday anymore or engage in light banter, only to initiate hang outs. I feel like she thinks I'm a quality guy, but my age is making her hesitate. She never been with anyone younger.

Considering all of the above.. do I still have a chance? Let me know what y'all think.

Your age has little to nothing to do with it. She's hanging out with you and putting herself in position to be seduced by you. She's doing her part, you're not doing yours.

Now, from the looks of your story, you currently just don't have the confidence to reel her in the way you would like. You're dropping "I'm interested" hints like a high school cheerleader. You're not being stand up, or up front, and you aren't making any forward motions toward escalation.

If you want to know what I think.. She began feeling insecure about the guy she's currently datings intentions with her, and so she began hanging out with you again to have another source of male energy for back up if its needed. Now if you had the conversation and the strength to actually make bold moves you could flip that to your advantage, but so long as you're baby stepping you'll be taking steps backwards.

Her: "hahaha you're stupid..." - What do you think that means?

Age isn't the issue, your confidence is. As a freshman in high school my girlfriend was a senior. And thats high school so its way worse in theory. Its a small community. Do you think she ever thought she would date a freshman? Since then, I've consistently dated women who are older. Younger girls are usually just good for a fuck buddy with me. There are some rare ones, but generally i'm just not into it.

Tell her you think she's "hot" - touch her arm when you say it. Eat off her plate at dinner without saying a word. Dream to the ice cream shop after dinner as a "surprise", don't tell her you're going. When you get there just say " I just wanted ice cream. you want some?" Swipe her butt and tell her she had some dirt on it (after you swipe it).. Be assertive bro. Invade her personal space. Cross the lines, and take risk. You won't get anywhere in life without taking risk.

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You have to to work on your game. She is giving you a second chance to seduce her.

I tried throwing out some signs of interest to see how she reacts, but no positive response. Such as...
Her: "What if I never find a man?"
Me: You got one right here (referring to me)
Her: Hahaha you're stupid..

^ You aren't really being challenging. Don't always be direct (even though Eddie might disagree) and play into these things. I like to think of flirting as an art form. An art where you imply you like the girl without rather stating direct interest. And a side note, if she mentions other guys, don't be jealous and don't react. Just move on and change the subject. If you really want to address it, just say "yeah, you guys should go out".

what i would have said
Me: Oh, I am sure the right guy will come along soon enough (smirk and escalate)

and move on.

You are going to have to bring out the big guns since I feel like this girl isn't taking you seriously as a potential lover. I went hard once I bedded my friend of 5 years. Always had sexual tension. She was in a relationship for 2 years. After she was out of that...I didn't play no games.

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Thanks for the insights. But any input on the below?

1. Anne usually pays for dinner (I've actually only paid once out 7 or 8 times we went out). I've heard the girl paying is good b/c it means she's investing. I've also heard it's bad b/c this is a girl's way of saying: this is not a date.

2. She has barely initiated convo since we reconnected, unless she's in my area and feels like seeing me, but is pretty available to me when I ask to hang. In the past month, we've exchanged 2 texts.. This was just last week.

Me: hiking in 2 weeks? i found a nice trail.
her: ok

Of course I'll follow up when the date gets closer. Considering there's this little communication.. is this bad?

3. My impression is a girl will not give you too much alone time (such as hanging out with your 4 weekends in a row, in the form of hiking, nba game, dinner, and museum day), if she's not interested. Even if you're a BFF/the straight-gay best friend, b/c chances are she's got other friends she'll wanna spend time with too. I do have some female friends (no interest) who I consider close friends, but I usually dont see them more than twice a month.

Your concerns are minuscule.

The point is.. she's hanging out with you alone in closed space. What are you going to do? Are you going to escalate? Are you going to seduce? Are you going to take the risky actions required to generate the attraction?

If a woman pays for my dinner, or I pay, if she shines my shoes, if I shine hers.. it makes no difference. If she's around me, she will be seduced period. None of that other shit matters.

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I agree with that's been said. She's giving you another opportunity to game her. At least you took some action and displayed your interest before even if it did make her awkward and stop contacting you for 3 months. The good news is that she knows where you stand by her re-initiating the interaction, she's implicitly agreeing for you to game her now. You don't want make it too easy for her, so you break rapport and qualify her. Make her invest and seek your approval as to why you should be in a relationship with her. Don't forget to escalate.

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See below, this was accidentily a dupe post.

Update:

Here are some tidbits from our meet up last Friday. The premise is Anne invited me to a friend's graduation.

1. met up at my house, but i offered to drive (my car) to the venue since she got lost on the way over. she counter-offered with letting me drive her car.. a 2015 Audi A6.

2. Since I knew she was seeing someone, I asked "why isn't he (Nelson) going with you?"
Anne says "I didn't invite him".

3. Anne is no longer dating Nelson. Long story short: they just didn't work out. She also pointed out that she wants a guy who is decisive (especially when picking a place to eat), doesnt spend most of his free time netflixing at home, will take her out, and someone whose over the partying stage. Someone who makes her feel wanted, really. All of which she's not getting from Nelson. As I heard these things, I was thinking.. "thats really all me.."

4. Anne doesn't really respond to my flirting positively. One instance that day: I had the chance to say what Mr. Assertive said above ("I'm sure the right guy will come along" with a smirk), and she kind of just laughed. I figure since she knows I still like her, she'll know what I'm implying is her.

5. Anne is not resistant to my touching. When navigating thru the crowd after the grad ceremony, I'd place my hand on her lower back until we get to where we need to be. I did this a number of times throughout the day. Also touched her on the elbow and thighs multiple times as I spoke to her. I accompanied her after the graduation for some errands. I walked pretty damn close to her. Noticed a bra strap was hanging off her shoulder and I slipped it back up. She didn't really touch me though. After the hug close, it seemed like she turned her face for a kiss on the cheek. I planted the kiss, then she smiled and said goodbye.

6. I said text me when you're home. She did. Also texted me the next day telling me about how she was excited that her old fav restaurant serves vegetarian food now. She only stopped going there b/c she went veggie. I didn't suggest to go there sometime, all I really said was just "congrats on the find". Wasn't in the mood to chit chat.

Done writing. I'll let you experienced PUAs criticize and analyze.

You gave in... Why?
What does nelson have to do with you wanting to escalate? And how does reminding her of her boyfriend help you in this situation?
Of course you were. You would of thought that no matter what she said. Its like horoscopes. People just want to identify with anything ideal in relation to them.


Pull it up = Nice guy helping out - Jokingly pulls it down = Flirty guy subtly implying his intention. You want to get her naked or do you want her clothed?

Other than the elbow touches what was different this day from any of the other days you hung out with her?

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