Hopefully I’m in the right subreddit for this question. But here’s the situation – there’s a woman in her early 40s (I’m mid 40s) who is a local TV anchor and goes to my church. I know that she’s single and she’s usually there with her parents and/or another woman – not sure if she’s a friend, or maybe her sister? Anyway, she’s there most weekends and we sit in pretty close proximity.

She’s drop dead gorgeous and my gut tells me that she suffers what a lot of really attractive women suffer from – lots of guys who would like to ask her out but probably don’t because they think she’s out of their league. I don’t subscribe to the philosophy that a woman is ever out of my league, but obviously the lack of guys approaching her works to my advantage. I could ask her out after getting to know her, but that’s the difficulty I’m having – finding that opening to get to know her.

We have locked eyes once and I smiled at her and she smiled back but that was it. Most weekends it’s difficult to even make eye contact with her.

I’m not sure what next steps I should take to get my “in” with her. I’m confident that if I could take her out for a drink or out to dinner that it would go well and she might end up liking me. But I feel like I’m at a dead end. Obviously I can’t just walk up to her and say, “interested in grabbing a drink?”.

Has anyone been in a similar situation? What advice can you give me? Thanks!

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