I’m Considering Giving A Guy I’m Not Interested In A Chance Because He’s Trying So Hard

There’s nothing less attractive to me than a guy who follows me around like a lost little puppy—I’m all about enjoying the chase. However, I ended my last relationship six months ago and the idea of getting back into the dating scene is daunting so I’m actually considering giving the guy who’s always had a crush on me a chance.

  1. He takes my BS. Sometimes I go for ages without responding to his calls or texts, but when I do, he’s still sweet, flattering, and makes me feel desirable. I know that no one wants to be with someone you think you can walk all over, but sometimes it’s good to know that no matter what, he’ll still be in my corner. Plus, I’m assuming that since he’s waited for me this long, there won’t be any pressure to speed things up. I can take things as slow or as fast as I want and he will happily oblige.
  2. He showers me with compliments. Anytime I bump into him when I’m out on the town, he compliments what I’m wearing and my smile, offer to buy me a drink, check that I’m OK, dance with me, and even tolerate my girlfriends. The effort is admirable.
  3. He knows my history and still likes me. He knows the type of guys I’ve dated—players, bad boys, studs, and all—but he’s never been deterred from thinking that he might one day have a chance. He always jokes and asks if I’m still with the guys he’s heard I’m dating, but I’ve never taken his advances too seriously. He just seemed like that guy who was around to boost my ego. Now I’m thinking that maybe there’s no harm in exploring and seeing if there could be something more.
  4. It will save me from the dating drama. If I decide to explore a relationship with him, it will save me from the fuss of going out on multiple dates where the guy might have boring conversation, annoying habits, or zero personality. I already know him, so I won’t have to go through the first date jitters of wondering what I’m in for. And if we run out of things to talk about while we’re out, we can always talk about our shared history.
  5. He’s a gentleman. Given that we have similar friends, none of them has had anything bad to say about him when it comes to how he is with girls. The general consensus has been that he’s a stand-up guy who treats women with respect and is loyal to a T. That is somewhat of comforting because there’s nothing worse than dating an a-hole.
  6. He’s easy on the eyes. He is actually cute, so the thought that I might get physical with him doesn’t necessarily put me off. I feel OK about it, though admittedly, it will be a task to shift my mindset from seeing him as the annoying guy who’s always chasing after me to a prospective guy that could be my boyfriend. Who knows, maybe getting to know him beyond our flirty conversations could uncover a fantastic guy that I end up being crazy about.
  7. He gets my jokes. While you could say it was because he was trying to get me to like him, I still think that he couldn’t have been pretending the whole time. I guess there’s only one way to find out if he indeed finds me funny.
  8. Being on a pedestal will be nice. At least for the honeymoon period, I feel like he’ll put me on a pedestal because he won’t want to mess up his chance at dating me considering he has pursued me for so long. That is a nice thought. To have someone catering to you, doing things you like, indulging your requests and trying to win you over sounds more appealing than trying my luck with dating apps or blind dates.
  9. He has a good sense of style. He has good taste in clothing. I feel that this is a huge plus considering how much I love dressing up. We can make an attractive pair when we go out on dates and even if we end up becoming a couple. It’s always good to know that your guy takes pride in his appearance and will make an effort.
Hannah is a twenty-something-year-old freelance writer, obsessed with reality TV, and all things sweet.