Should you ask for a second date if she seemed skeptical about your goals?

The moment that stung is usually the most specific thing she said, so look at it closely. Did she question whether your plan is realistic, whether you have started, or whether it is actually what you want? Each of those points to a different thing. Questions about follow-through suggest she wants to see action. Questions about whether the goal is really yours suggest she is checking for seriousness. A direct question about your timeline is ordinary first-date vetting.

Also notice how she was when she said it. Was she leaning in, asking follow-ups, teasing a little, or did she go flat? People who are interested often challenge you because they want to see how you respond. People who are done often just stop asking questions. If the rest of the evening had real back and forth, one skeptical comment is not much to go on.

If the skepticism came with an open question you never fully answered, your follow-up is a chance to close that loop. Pick the one thing you can say plainly and honestly, such as what you have already done toward the goal or why it matters to you. Keep it to a sentence or two. Then move on. Going back over the same point in more detail reads as still stuck on it.

Do not invent progress you have not made. If your answer is that you are still working toward it, say that. People can tell the difference between someone who is building something slowly and someone who is performing confidence, and the first one is more attractive to most people who would be skeptical in the first place.

A second-date request works best when it stands on the rest of the evening. Reference something she actually enjoyed, a place you talked about, a story she told, and suggest one concrete next thing. Leave the goals question out of the ask. If you bring it back up in the same message, you are inviting her to re-litigate the point before she has decided whether she wants to see you again.

Give her an easy way to decline. A clear suggestion with a specific day or two is more useful than an open "we should do this again sometime." It lets her say yes without committing to a long conversation, and it lets her say no without feeling she owes you an explanation.