I'm a young straight man in my mid 20's in a large US city. I went out for drinks with a first date with a Tinder match about 2 weeks ago. I thought it went exceptionally well. Made her laugh a decent bit, solid chemistry, interesting conversation for 3 hours until it was late on a weeknight and she had to catch a train home. Admittedly, I was pretty awkward when kissing her at the end, but no big deal I thought. I texted her 2 days later saying I enjoyed it and wanted to see her again. After a day or so delay she replied that she had a good time but wasn't feeling it. I was super bummed because I thought it had gone really well overall.
Fast forward a few days and she texts me again telling me she keeps thinking about me and was thrown off by the end of our date, but has changed her mind and wants to see me again. I excitedly accept and set up a mini-golfing/bar date for a few days later.
2nd date also goes great except for a hangup at the end. Another very interesting conversation. Girl seems very intelligent, ambitious, thoughtful and honest, which are huge turn ons for me. She starts holding my hand in the bar as we're sitting and speaking very closely. We make out a fair bit and I'm having a great time. She seems to be too. It's getting a little heavy for the bar, so I invite her back to my place. She accepts. We keep kissing for a minute, until suddenly she's crying and changed her mind about coming home with me.
She tells me she semi-recently (a few months? not sure) dumped a guy because although he was a good guy, he wasn't ambitious enough for her. She says I'm genuine and nice, which reminds her of him, and I guess she feels guilt for ending the relationship.
She says she needs to figure out what she wants and is clearly distraught. I rub her back and give her hugs trying my best to comfort her. Once again I'm bummed but I tell her to please not feel pressured about seeing me again because I'm starting to like this girl and I feel bad for her since she's obviously conflicted. I want her to be happy and comfortable seeing me. I walk her to the train station and hope for the best, although I expect her to text me saying there will be no 3rd date.
To my pleasant surprise, the next evening she texts me thanking me for being cool about the situation and saying she had a great time. So I invite her to my place for wine tomorrow. I'm really looking forward to more great conversation with her because she seems quite insightful and I appreciate her self aware thought process. It also seems likely things will physically escalate, which is exciting, but worrisome because of how things went the last 2 times I kissed her.
Not sure how to play this one? Any analysis or advice appreciated.
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