I have a situation that is driving me nuts! I am in my late 30s, divorced with a teenage child. I have I guess what you would call a crush on someone in his early 40s. He has two children who he is raising alone. We live in the same area so I see him almost everyday. He is constantly giving off the classic flirting signs, i.e. staring, gazing, smiles, small talk, etc. He has been doing this since last summer but it seems to have gotten stronger. Once I was talking to another man and he raced over to where I was standing to find out who he was. Another time I was talking loudly on the phone and I saw him eavesdropping behind a fence. I do flirt back by giving him eye contact and waving and saying hi to him. He is a VERY confident, outgoing person and I am totally confused by his signals and ultimately his motives. I feel like we are in grade school playing the staring game. This is so unlike his personality to be so shy. While it is sweet, I am getting frustrated by the whole situation. Btw, he knows I am divorced and I made it known recently to someone close to him that I am not dating anyone right now. I can't understand why he hasn't asked me out yet. Also, I am very shy and would never make the first move. Any advice from the guys would help. Thanks!
Most Helpful Guy
This easy. You live close by and you're a single mom? Next time you talk to him, stay standing there when there is a silence in the conversation, wait very calmly, make no move to end it, and wait for the talk to start back up. This is a signal that you want to be with him.
Hey guess what? You need some help around the house! If only you knew a strong man who could drop over and spend a few hours working in your back yard (for example). You can't afford to pay but you would certainly be happy to prepare a home cooked meal for any kind gentleman willing to help you out. You could even reciprocate in kind and do some washing or cleaning for such a good samaritan.
So he comes over to your place and spends a few hours helping you, then you go over to his place and help him. The important thing is that you never get nervous when there's a silence, you just stay where you are and wait calmly. This shows that it's not the words that are keeping you there, it's him. A calm silence will advance your cause better than nervous words.0