This is a lot but I wanna include the context so people understand why I’m having a hard time with this. I’m (36M) suddenly back in the dating pool after my wife of 14 years (HS sweethearts and we dated before that too) decided that she’d rather go live with her coworker back in February, and I’m struggling with the most basic of things when it comes to dating and seduction. I was totally blindsided by her betrayal and I nearly killed myself when it all when down, but I got past it thanks to some amazing friends and family, and I’ve spent the whole year working on myself, going to therapy, and once I finally felt healed enough, trying my hand at casual dating. I used to feel like I lucked out and never had to really experience the dating games, other than with my now ex-wife, and it feels like I missed out on some crucial skills because I’ve been in the same relationship since HS up until this year. Now I see how unlucky that really was, and I feel like such a fish out of water. I need some help navigating a new potential thing, and interpreting what I perceive as flirtation, I suppose.

I had a few flings that went nowhere recently. My best friend is now trying to hook me up with a female friend of his. They have no history other than the fact that he was friends with her ex at the time, but she has also been single for most of this year, and he insists that we are a perfect match. I finally met her at a party I hosted recently, and I’ll go ahead and say it…my friend was not wrong. This girl checks all my boxes. There was immediate chemistry, and I caught her looking at me an awful lot, and laughing at everything I said. As we got to know each other over the next few social events, I found out that we even share almost every common interest too, from anime to playing guitar to the type of video games we play. Until today, however, I didn’t even have her number. She would just communicate with my friend and then I’d see her when she came over. My friend talked me into installing Snapchat, which I’ve never used, and then told her that I wanted her Snap. I was worried when he said this, because to me that seemed very forward, and then I got kinda bummed when she replied to him with “what are his intentions?” I decided to drop it because I thought she was weirded out. My friend says she’s just a very shy type of person.

A few days later, she asked my friend and some other friends to help her move to her new apartment. My friend enlisted my help, and then intentionally changed his plans so that it would be just me helping her, which I did, and she was very appreciative. She even made it a point to call me out in a positive way and told all our friends about what a huge help I was, but still, she didn’t reach out to me directly.

Later, my friend (props to this epic wingman btw) tried a new approach. He invited all of our friends to a group chat, and I finally had some communication with her outside of social events. It started slow, but there’s been a bit of playful banter between us, and then last night after everyone else stopped responding, she and I just continued on for several hours, which eventually turned into us sending each other pics of our guitars and our cats and stuff, all of which included her in them and she took while speaking to me.

This morning, I got a text from her directly. Not as part of the group chat. It just said “here’s my Snap btw, I think you’re cool enough to have it now ☺️”

So, I added her, and it took her like 6 hours to add me back. When she did, I waited until I was off work, and sent her a snap just asking her about a particular anime she mentioned to me (legit question as I couldn’t recall the title). That was a few hours ago now, but she hasn’t responded yet. I figured she’s busy, but then my friend told me that she had texted him just a while ago to tell him about some family drama.

So now, I’m just like…idk. She’s obviously more comfortable talking to him due to already being friends. I know for certain that she isnt just into my friend, before anyone asks, for a multitude of reasons that I won’t go into here. But I’m confused, because it’s like she wants to talk to me, but also not. Is she just being kinda shy, or what? I feel like I’m reading way too much into everything, especially aince this is brand new, and obviously it feels so confusing because I don’t know what the hell I’m doing. My friend insists that the text she sent me was definitely flirtatious, and that I should try to be more flirty, but I really don’t know. I feel like I’d be coming on too strong and scare her away, ya know?

I’m just hopeless at this and need some guidance. Thank you all for reading this.

1 comment
  1. It sounds like there is definite mutual interest and attraction here, but she does seem on the shy side. A few thoughts:

    – Take things slowly. The fact she’s opening up more is a good sign, but going at her pace will be important to not scare her off.

    – Keep conversations light and fun through text/Snapchat. Share little things about your day vs deep conversations for now.

    – Suggest a low-key hang out just the two of you, like grabbing coffee, to connect without others around putting any pressure on her.

    – Compliment her personality and interests vs her looks too much yet which comes across stronger.

    – Respect response times – she may need processing space. Don’t double text right away if no reply.

    – Try bringing up a funny memory from your conversations to pick things back up if she’s slow responding sometimes.

    – Let things progress naturally vs trying to force or overanalyze. Go with the flow and let chemistry build gradually through quality time.

    It seems you’re doing well so far. With patience and understanding her shy nature, this has potential to really blossom if you make her feel comfortable going at her pace. Keep letting your genuine self shine through.

Leave a Reply
You May Also Like