That's the question, two of them, actually, that I answer today on Boundless. One woman wants to know if it's OK to ask a friend of hers to ask the guy she likes if he likes her. "Is this like the fourth grade?" she wants to know. Well, yes. She wonders if it's "OK to use a mentor or mutual friend in this way?" In a word, no. But I do give her more than a two-word reply:
There is a way to include older, wiser married believers in your life, in the context of a church body, that provides opportunities to talk about your desire for marriage and even your interest in a particular man. But in that setting, the goal should be accountability toward spiritual maturity, as well as protection, not orchestrating a date for Friday night. What you describe sounds like manipulation — trying to influence events to your favor and will. And it doesn't typically end well.
The second woman has been friends with and liked a guy for 10 years. Ten. She wants to know, "Am I wasting my time? Is he never going to see me in that light? Should I stop asking him to hang out? I've met his family and spent time with his sis, and she said he is horrible with contacting people. What should I do?"
It's painful to think that 10 years will have been fruitless in this area, but it's time to face facts:
Go with what you know — he's not interested — and stop throwing good time after bad. This relationship is not going to lead to marriage. What's worse is that by hoping he'll change, you're probably missing out on other good men who would make godly husbands. And you're growing older all the while, possibly squandering your season of marriageability. This is a stewardship issue for you.
You can read the full questions, and my response, in "Taking the Lead."