Dear Annie, I've been exchanging smiles and hellos with an attractive young woman, who I usually see jogging past my bus stop on my daily workout.
I would love to get to know her, but I'm not sure how to arrange it. I think that she lives a couple of blocks from me, but I don't even know her name, let alone her address or phone number.
I wish she could see me in dress clothes instead of my morning jogging clothes. How can I "coincidentally" bump into her without seeming too obvious? What would be the best strategy with which to approach her? Claude
Any time you introduce yourself to someone new, you are simply exploring possibilities. You can't possibly predict what the outcome will be. Because so much about a stranger is unknown, your best bet is to proceed as a if you are a detective who makes use of clues and signals to guide you as you move forward.
You say she's an "attractive young woman," so I'm going to assume that she's significantly younger than you. If that's the case, she might feel comfortable smiling and returning your hellos because she perceives you as a friendly older—read fatherly—guy.
Don't assume that a woman is interested in you just because she smiles and exchanges hellos with you. She may simply be a happy person who is friendly with everyone around her. On the other hand, she might be thrilled to finally have a chance to meet you. It's up to you to discover if she might be open to your advances.
All you need to do is temporarily alter your morning routine. Dress in business clothes and wait for the bus at the same time that you usually see her. Plan to ride the bus for a few minutes, disembark and return to the original stop.
Since you're already familiar with each other, it shouldn't be too much of a stretch to go from smiles and hellos to introductions. You'll appear more confident if you smile and don't shy away from eye contact with her.
Check to see if she's wearing a wedding band or engagement ring on her left hand while you're introducing yourself. Ask her how her day is going. Listen carefully to her answer, as you may learn everything you need to know from her reply.
If she mentions a husband or boyfriend, continue the conversation with small talk about your neighborhood, the weather or the reliability of bus schedules, for example. If she talks about her kids, ask a benign question about her husband, perhaps about how long she and her husband have lived in the neighborhood. You'll quickly find out if she's single and possibly available.
You can tell her why your morning routine is different that day. Mention that, although you routinely jog by, you happen to be waiting for the bus because of an unusually timed important meeting. She doesn't need to know that the object of your meeting is to make her acquaintance.
Take it slowly. Women tend to need time to warm up to a man they have just met. If you have a light and playful attitude, she'll be more likely to relax and enjoy your company.
If she seems to be single, available and engaged in conversing with you, ask her where she likes to hang out nearby. Tell her about one of your favorite neighborhood spots or activities. If she seems interested, offer to accompany her there in the near future. If she appears ambivalent, you can hand her one of your cards and tell her you'd like to stay in touch.
Whether she wants to get to know you better or prefers to move on, you'll both save face if you end your conversation on a polite and dignified note by telling her that you're delighted to have met her.
You'll greatly increase your opportunities to find love if you plan to meet women with the goal of simply exploring whether there is a possible point of connection between you two. If you're like most people, you'll be more confident and appealing if you don't have the pressure of feeling as if you failed if you don't achieve the result for which you were hoping.