She is not to young for boyfriends but this boy James seems like the wrong type of guy for her to date with. Especially if it’s her first time dating, this will leave an impression on her and you also mentioned that he has multiple girls at a time. It’s quite possible he just wants sex which unlike dating I wouldn’t recommend for someone her age. Just my thoughts though.
She is too young to date. However, she is not young to have a crush on a boy, and she isnt too young to like bad boys. I would be careful how you handle it, and make sure you handle it based on your daughter and what you know about her. An example my daughter was very rebellious at that age. Which means when we told her "no" she would do it. Therefore we tried not to use the word no, and tried harder to make her make the right decision. My son on the other hand understands when his dad says "no" that is "no" and so my husband was direct with him. "No" you arent able to do that because...".
Parenting is hard and every child needs a different touch. Plus girls are harder. No matter what the best approach is always to make sure you have an open communication with your daughter. Let her be able to come to you with things without getting upset at her. Let her be able to discuss things with you, with out feeling like you are going to judge her. At the same time stand firm when needed. Not sure this helps but hope it does.
From having teens age 15 and 16, I found that 'having a girlfriend' or 'having a boyfriend' at 14 usually means they are doing snap chat (if you allow it), texting or face timing each other. Might meet up on X box. Might get together in a group event. I'm okay with all of that and think it's normal. Dates where they go out just one on one at 14? Once they are a freshman in high school which some 14 year olds are, you'll see it more. Now, the boy you are talking about? No way. I set boundaries for my kids about what's healthy and what is not. The boy sounds to partake in unhealthy activity. You do have to be careful not to create the romeo and juliet thing where you say they can't be a couple and that makes her want it more. Which DOES actually happen. Someone gave me advice when my kids were still in elementary school. They said that during those teen years you are now in, the key is to keep them busy with their activities. My kids are into sports and band and all of that. They are time consuming. Key club is a good high school activity that keeps them busy. Theatre. Whatever it is that she likes, encourage her participation. Less time means less time to get in trouble.
I also learned that if I don't react, stay calm and don't immediately panic and start lecturing, my kids will tell me more. That's what we want. You want to be an open door. And if they tell you something in confidence, don't share it with others unless someone is going to get hurt.
We did the thing too about exiting. If they are somewhere and something starts to go down, they send me a text of a single letter or X. I call their phone and say something has come up at home and I have to come get them. It's their safety net and their out. And then I can't ask any questions. They can tell me why they had to leave or they don't have to. Just so they WILL call when they feel they want out of a situation.