The majority of things that people on here label as "red flags" aren't. they are often minor things that are easily taken care of.
He is likely just nervous from inexperience.
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I think he’s just insecure and really wants to get to know you which is why he keeps asking if things are going well. Take it slow. If he keeps asking for reassurance after that then just drop him…who knows what he’ll do if you decide to stay ( IF he keeps asking for reassurance).
Girl, if I took you on a date I would know it's going well and I wouldn't need to ask.
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Sounds more of an insecurity/nerves than a red flag. I’d give him another shot if no dealbreakers came up.
No he’s young and probably immature and wants to make sure things work out
He is probably not that secure and needs reassurance
Probably just nerves
I'd say nerves
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