Should I let this one go?

[Hippydippu]

I met a guy at a dinner through a good friend of mine. I thought he was cool and asked my friend for his insta and dmed him if he would like to get coffee sometime. He said he would love to and was thinking about asking himself. He planned the date himself. He replied late usually but I didn't think much about it. Our first date went well and he even said at the end that he’s glad I asked him out because he would have been way too scared to. He asked me out on a second date the same night and that date went well also. After the second date he didn’t answer my thank you message for three days but finally got back to me and asked me for a third date. The third date went very well also. I thought he would kiss me at the end but didn’t. He ended up coming back to get me since he said he was hungry and on the way back he said he wasn’t really hungry and just wanted to spend time with me. The next day we were texting and I called him out on not kissing me and he said he was just really nervous. He was supposed to come over the day after that but he cancelled. I asked him to hang out one day and he said he couldn’t but he did reschedule. During the fourth date I asked him what he was looking for. He said he wasn’t sure yet. I took that as a nothing serious. I told this to my friend and she admitted that this guy had a giant crush on her around 5 years ago to the point where she led him on and things did not end well and they stopped being friends. They were cordial now though. Looking back at it I would talk about her on all of our dates. I even told him after our second date that she would probably get married soon. He texted me a meme a few days after the fourth date but no one said anything since. It’s been about a week. My friend tells me now he was a player back in the day and knowing that and him not even kissing me makes me feel like he wasn’t into me at all. Should I let this one go?

[JoePro_]

He sounds undecided, flippant, and flaky, to be perfectly honest. I wouldn't keep all your eggs in this basket. Keep your options open and explore those options until he convinces you otherwise. If he seems to have a problem with you out dating others, be straight with him. Let him know that you like him, but that you're not convinced he liked you in the same way. That 3 days in between talking to each other, that memes instead of conversations, and that his indecisiveness on a variety of things hasn't convinced you that he was very serious about wanting to date you. Then go from there based on what he says, how he acts, etc. However, I wager you probably shouldn't see any blowback. He might be disinterested in you as a dating prospect, but still might just be testing your boundaries for kicks. Who knows really. Regardless, I'd move on. Best of luck!

[Hippydippu]

Could his undicicveness be due to me talking about my friend so much and him realizing how close I am to her? If that may be the case I rather just rest it since he would probably have to see her around if he is with me.

[JoePro_]

Maybe? Maybe not? I would ask "Should it matter if you talk about your friend?" And if it is "Why is it bothering him?" There's still a maturity issue I'm seeing with the context you've provided. Even if there is something bothering him, at least based on what you've provided here, if he were truly interested in you, your friendship shouldn't be stopping him (unless you had friends who were totally not friend material). And let's say he does have a problem of some sort with her, are you willing to end your relationship with her to be with him? If she's a legit good friend, I would hope not. There's just a lot going on here, that I would say move on. Just my thoughts. But if you're seeing something that we're not (since we're not there or part of those relationships), I would say use your best judgement.

[Hippydippu]

Thank you!

[DarkWinterNights]

There are a lot of factors at play here. It sounds like the two of you get along very well, which is a good sign. But it seems like there are other people involved that are either intentionally or unintentionally trying to sabotage the potential relationship. Because the first couple of dates were quick, natural and fun. Afterwards, either he has someone giving him advice or he himself is overthinking things. Your friend could also be an indirect factor. But a lot of guys, when they get rejected or get over someone, it’s hard to see them in that light again.

[Hippydippu]

As in he wouldn’t be comfortable around her?

[boobliker]

Do what your hart tells you to do not what look or feels right.

[Billlewis]

Dump him immediately; you deserve better.

[Anonymous]

You can try again

[Hippydippu]

Do you think he was ever into me or just bored?

[Opinion Owner]

Yes, you’ve had four dates

[laly520]

move on