Hey Alex, I have a very specific Twitter dating question, and I’d appreciate your advice.
There’s a single woman I find very attractive, kind of a Milfy type, and we’re mutual followers on Twitter. We each have a few thousand followers, so we’re not strangers, but we don’t actually know each other personally. She posts frequently about politics, particularly the midterms, and football and has Venmo listed.
Here’s the interesting part: I live in Jersey, she lives in Kansas, and my job will likely have me traveling to her area in about a month. I don’t have the exact dates yet.
My goal is to eventually ask her out/hook up while I’m there, but I want to approach this strategically without coming on too strong.
A few questions:
Should I start engaging with her tweets publicly to build familiarity, or just go straight into her DMs?
If I DM her, should I open with something about the midterms, the Chiefs, or mention that I’ll be visiting Kansas for work? What would you actually say?
How do I transition from talking about our shared interests to flirting and eventually asking her out?
Most importantly, how do I signal romantic interest while maintaining plausible deniability if she’s not interested?
The last point matters because Twitter is a very public environment. I want to be confident and direct without being so forward that I risk having an awkward DM screenshotted and put on the timeline.
Given that we’re mutuals but don’t really know each other, what would your exact approach be, from the first interaction to potentially getting a date?
