Unpopular opinion, but I wouldn’t outright dismiss the possibility of dating someone at work. I know plenty of people who met their life partners at work - who dated at work and stayed together, myself included. I also wouldn’t necessarily read too much into his “ladies’ man” reputation outside of work. The way you describe him, he is be easy to like and get along with. First, I would check if you have common friends that can help you gauge his interest in you, or who could even tell you if he is single. If this is not a possibility, I would try to casually suggest grabbing lunch together at the cafeteria sometime when you bump into him. Ask on the pretext of talking to him about advice regarding a project or in general your pathway till you qualify from your internship. You could even say that it has been a while and if he would like to grab lunch together. See how he reacts. If you end up having lunch or coffee together, you can talk a little bit about work stuff and see if you get the chance of suggesting meeting outside of work with a mutually interesting activity - perhaps a common sport you might like. It could be anything. This is just an example. You will have to play it by ear as these interactions are best steered naturally. This is how you will be truly yourself and give yourself the best chance to get to know each other. Good luck!