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When when do you guys believe persistence for a woman passes into devaluing yourself?

Backspin2
Throughout my life I've heard of stories and also seen first-hand guys asking women out multiple times until they say yes. A lot of these resulting in long-term relationships and even marriage. Even if I deeply desire somebody, asking them out one time is enough for me. I look back in the past when I would ask the same girl out multiple times and yes sometimes I got the date, a couple of occasions a relationship. However, looking back on it now I feel like such a loser and a beggar for that. I feel like there are much more worthy things to be persistent towards then somebody's affection. What are your guys thoughts on this?
When when do you guys believe persistence for a woman passes into devaluing yourself?
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