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LeopoldBloom · M
It depends if he has a history of lack of success with dating, or if he's had one or more fulfilling relationships. In the first case, he may want to ask people who know him what they're noticing about him that could be off-putting as he could be unwittingly sabotaging himself. I'm thinking things like only talking about himself, or showing signs of jealousy prematurely, being too controlling, etc.