How to ask a younger man out for date?

I am conscious of my age and reluctant to make a first move

Summary: While it is always romantic that a gentleman ask a lady out, not all circumstances in dating are such that this is possible. That is why I always recommend that this rule should be ignored when needed even at the expense of a woman being perceived as aggressive. Read below how I tell an older woman to ask a younger guy out because he cannot ask her out due to his unique situation.

Photo of an older lady hitting flirting on a young dude bloke

Allison writes, "I am very attracted to a younger man where I shop. I also know that he is attracted to me. All we do is smile a lot at each other and say hi. This has been going on for about 9 months. I am a very attractive woman in my early 70's. I look like I am about 50. I have been waiting for him to ask me for coffee. I have not approached him mainly because of my older age. I am guessing he is in his 50's. He is the general manager of the store. I am a widow and I have found out he is single. I do not have a problem with my age or how I look. Maybe it is against company policy to approach me for a date? Since I am used to having the man make the first move, I am not comfortable doing it myself. What do you suggest I do and if I do start the conversation should I mention any thing about me being older, probably not? Any suggestions will be appreciated."

Almost all corporations and workplaces have very strict policies about interaction with customers and colleagues. You can imagine that in this economy the last thing he wants is to jeopardize his job because if he misunderstood a customer's intentions and you complained to the company, he will be fired right away.

Due to these circumstances, I would say that it is perfectly appropriate for you to make the first move. You can say something along the lines that you enjoy chatting with him while you visit the store but there are a couple of things that you would like to chat about in peace and would he be interested in having a cup of coffee/drink at a convenient time. Hopefully he will accept it.

I do not think that you need to disclose your age at any point. Most men do not expect you to. Obviously, if he is interested in you more, the first interaction will lead to more and as the conversations start, he will eventually figure out and so would you his age and attitude towards older women. You do not have to lie or avoid the question and be truthful when asked directly but there is no need to volunteer that information the way you wouldn't volunteer your bank balance or how you bought the dress that you are wearing 75% off.

I have a crush on a younger colleague

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