Second date - nothing happened

[warus]

So I met an older woman (10+ years older than me). She knows my family and I know hers as we live close to each other and my family and hers are pretty good friends. I hit it off with her one Friday while partying (talking and after bars closed we went to one still-open venue alone and talked). I initiated that we go somewhere else and she was in. It wasn't all that friendly as it was a lot of flirting but nothing else happened. We then started talking on IG and she was very receptive and wrote long messages and asked a lot of questions, even initiating the conversation with me 90% of the time. I invited her out and we went for drinks. We were on a date for 6 hours. Again, not really friendly but not really flirty as well, sort of a grey zone. We went to another city as everyone knew us in my city and she didn't want people to start rumors, she wanted to keep this quiet. She did mention the age difference a few times, but I handled it well, making her laugh on those occasions. Nothing happened on the date as well as her body language was really closed off but the conversation went extremely well. I flirted, she also flirted back a bit. Sometimes she would give me a hint that it was all friendly, but then at times, it was definitely more than that.

I was left confused but I reached out after three days and invited her out again. She couldn't do the day I suggested but she immediately suggested an alternative so today we went out for drinks. However, I'm not sure what to make of it. Again, she sometimes suggested it was not all friendly and looked at me differently, but when I would try to physically escalate she wasn't very interested in it. The conversation somehow went the way where we were talking about alcohol and she said she doesn't usually have anything at home, only wine. She asked me to sing something as we talked about music after that and I saw it as a great opportunity to say - Not here, only if we open that bottle of wine :). She responded with: "let's take it slow. I don't want us to go into my apartment", and even mentioned that there were only 2 guys at her place, and they were her boyfriends. She then once again said, "take it slow" and we continued talking. Then after some time, she would start talking about how great she feels being single and blabla, but then again starts throwing some flirting later on. I didn't go for the kiss at the end after hearing her say the thing about being single. What the hell is happening here and how to continue going forward?

[Wiseman2]

7 minutes ago, warus said:

. We went to another city as everyone knew us in my city and she didn't want people to start rumors, she wanted to keep this quiet. She did mention the age difference a few times. when I would try to physically escalate she wasn't very interested in it. Then she would start talking about how great she feels being single and blabla, 

How long have you known each other? How many dates have you been on?

She seems somewhat interested but doesn't seem in a hurry to "escalate" or hookup.

She also seems somewhat embarrassed by the age difference if she wants to keep your dates a secret. 

Maybe she's just uncomfortable in general or with too much too soon? 

[Andrina]

Well, you've made an effort 3 times now, so how about you sit back and see if she invites you out? If she does, and there is still not a comfort level of things progressing like holding hands, etc., then ask her if she'd consider going on actual dates instead of meeting up as friends.

I'd guess she's wrestling with liking that you have a crush, but feeling uncomfortable with the age gap. I know I'm one of those women who wouldn't feel comfortable dating a guy more than 5 years younger than me.

If she doesn't ask you out, I'd take it as she's either just not that into you, or is not comfortable with the age gap, so it's best to let things fade with her. Don't convince her not to try to be comfortable. If she's not okay with it now, things might even worsen in the future, as she might start worrying too much about how her wrinkles and other aging differences are appearing a decade before yours. 

[warus]

Just now, Wiseman2 said:

How long have you known each other? How many dates have you been on?

She seems somewhat interested but doesn't seem in a hurry to "escalate" or hookup.

She also seems somewhat embarrassed by the age difference if she wants to keep your dates a secret. 

Maybe she's just uncomfortable in general or with too much too soon? 

About a month ago, and I just came home from the second date. 

What's bothering me is the constant shift between friendly and flirty. She is receptive to my flirting and even flirts back, but physical escalation is almost at 0. She seems really closed off. I tried the: I can read from your palms, and she didn't want to give me her hand so I played it off casually, but still.

[warus]

2 minutes ago, Andrina said:

Well, you've made an effort 3 times now, so how about you sit back and see if she invites you out? If she does, and there is still not a comfort level of things progressing like holding hands, etc., then ask her if she'd consider going on actual dates instead of meeting up as friends.

I'd guess she's wrestling with liking that you have a crush, but feeling uncomfortable with the age gap. I know I'm one of those women who wouldn't feel comfortable dating a guy more than 5 years younger than me.

If she doesn't ask you out, I'd take it as she's either just not that into you, or is not comfortable with the age gap, so it's best to let things fade with her. Don't convince her not to try to be comfortable. If she's not okay with it now, things might even worsen in the future, as she might start worrying too much about how her wrinkles and other aging differences are appearing a decade before yours. 

Second time actually, this was our second date.

[Batya33]

Why would she want to keep it a secret that you're spending time together on a date?

[LotusBlack]

Are they actually dates, though? Are you on the same page about the context of your meetings? I’d clarify that, first.

Also, I am sometimes like her when I want something but feel incredibly uncomfortable within myself or with my feelings. I give myself outs when I feel too exposed or vulnerable. It’s a way to keep some distance while I figure out whether I will be able to be comfortable with something or not. She may be doing that, too.

I think, in your shoes, I’d move on.

[Wiseman2]

5 hours ago, warus said:

 She is receptive to my flirting and even flirts back, but physical escalation is almost at 0. She seems really closed off. 

She seems lonely but not that interested. Especially in moving as fast as you would like as far as getting physical. 

[itsallgrand]

My take would be she enjoys the attention but doesn't want to hook up. 

[warus]

10 hours ago, Batya33 said:

Why would she want to keep it a secret that you're spending time together on a date?

Because we live in a very small town where everyone is connected, so if people saw us it would actually bring about a ***storm (no joke), so this just makes it easier. I actually agree with it because I don't like gossip and stuff as well.

[kim42]

She said she wants to take it slow so I wouldn't suggest dates at your or her place for now.

Maybe she's not sure about the age gap or she just enjoys the attention but doesn't want to take things further.

Did you communicate after the second date? Is she interested in meeting up again?

[warus]

23 minutes ago, kim42 said:

She said she wants to take it slow so I wouldn't suggest dates at your or her place for now.

Maybe she's not sure about the age gap or she just enjoys the attention but doesn't want to take things further.

Did you communicate after the second date? Is she interested in meeting up again?

I actually messaged her during the date because we had an internal joke. So after I got home I noticed she responded to that saying to drive home safely. I told her I just got home and she said good night and sleep nicely. That's it. I'll definitely wait for her to contact me first, she is actually going abroad for a week on Friday so I won't be able to meet up with her anyway.

[Wiseman2]

3 hours ago, warus said:

Second date - nothing happened

What exactly were you hoping would happen? If she is self-conscious about the small-town gossip and age difference it doesn't seem like she's comfortable. Since she'll be away, reflect what you would like to see happening and if this is even viable. 

[warus]

1 hour ago, Wiseman2 said:

What exactly were you hoping would happen? If she is self-conscious about the small-town gossip and age difference it doesn't seem like she's comfortable. Since she'll be away, reflect what you would like to see happening and if this is even viable. 

I'm not sure exactly. A kiss would be enough. Or even the opposite. I would be completely fine with her not wanting anything, but explicitly saying that she wants me as a friend. But being in that grey zone where she is flirting and saying some other things but then goes completely friendly is what's bugging me.

[smackie9]

I say she's just enjoying the attention...I doubt it's going to get to the next level. If she wants to keep it a secret, that's a big red flag.