Question

I met a man at a work function. Told my best friend about him and when I said hai name. It turns out he was as her ex next door neighbor. She texted him and told him he had met her best friend and I thought he was hot. He replied oh mercy. He loved a pic of me and her she posted on Instagram. 2 months later he sent me a request to follow me on Insta. She posted another pic of us last week
And he loved it. He views my stories and loved one of the stories. I wound like to think he is interested. We are both late 50s.

Answer 1

It does sound like he’s at least curious — follows, likes, and watching stories are common early signs of interest online. They don’t guarantee anything romantic (some people just like photos or enjoy peeking), but repeated engagement + the follow request are encouraging.

How to move it forward (short, practical steps)

1. Follow back (if you haven’t). It’s a neutral, friendly signal and opens direct messaging.
2. Respond to a story or like/comment a recent post. Pick something specific (a place, outfit, or caption) so you give him something to reply to.
3. Send a light, direct DM within a few days. Because you have a mutual connection, you can use that as an easy opener.

Message examples you can adapt
- Casual/friendly: “Hi [Name] — we met at the [work event] a while back. Your neighbor [Friend’s name] mentioned you guys were chatting — nice to connect here!”
- Playful/flirty: “Oh hi — I see you liked that pic. You’re on my followers’ VIP list now 😉 How’ve you been since the event?”
- Direct/forward: “Hi [Name], I enjoyed meeting you at the work event. Would you like to meet for coffee sometime to continue the conversation?”

If you prefer to start smaller, reply to a story with something specific: “That restaurant looks great — what did you order?” or “Love that jacket — where’d you get it?” That invites a natural back-and-forth.

Other tips
- Look for reciprocity: if he asks questions, tries to continue the conversation, or suggests meeting, that’s stronger evidence of interest.
- Be clear about what you want. At our stage in life many people appreciate directness — if you want to meet, say so.
- Stay safe: meet in public the first time, let a friend know plans, and move at a pace that feels comfortable.
- Use your mutual friend if you want an easier route: she can introduce you in person or encourage him to ask you out.

If you’d like, tell me which tone you prefer (casual, flirty, direct) and I’ll draft a message you can send.