Triple texts) and wants to talk on the phone every other day. He’s already dropping hints about Valentine’s Day. As a fello introvert that needs space this is a bit much for me. Is this too much or obsessive? Potential red flag? It kind of feels like a lot of pressure and chore to respond or make all this time to talk so early on. I want to take things slow which I expressed but everyone’s version of that could be different. My last dating experiences also make me a very cautious person. This guy seems nice but disposition wise a little intense as well which makes me more cautious.
On the opposite end of the spectrum, I’ve been talking to another guy and we have been messaging for a few months. We’ve talked on the phone a couple times and hopefully will be meeting soon. He’s more more lax and chill and respects my space. He seems a bit more normal which makes me feel more at ease.
It's not a red flag, the guy's just excited that he met someone he likes, and he knows how difficult it is to get a girl's focus and attention online with other guys also doing the same, so he's probably just happy. "Red flag" is a trendy word right now, just like "narcissist", and "gaslight." See how negative they all are? These things have always been around (well, "gaslight" since 1940 when it was first conceptualized in a film), but we live in a world today where lots of people are interacting online, but everyone has a super sensitive filtering system.
He makes you uncomfortable and that makes sense, and it's your right to feel that way. He needs to chill. He's going to spook you, and a bunch of other girls, too, probably. Dating is very slow, and very low-commitment now. People really don't trust each other and are being careful. If you two did have a lot in common or aligned, do you think you would behave differently (want more), or even in an ideal situation, would you still be reticent? You said your last dating experience has made you cautious. Can anyone break through now? I'd ask yourself that.
The other guy you mentioned, he doesn't feel good about himself right now, and he's low on funds and low on morale. A lot of people (especially guys, who so-identify themselves by their work) feel like this, and it also makes sense. But he's on the opposite end of the spectrum, here. You need a guy in between, lol. So, slow one guy, and speed up the other a bit. (Just take longer to respond to the second.) If neither really get you motivated, maybe neither is right or worth pursuing?