Guys, Is it okay for a woman to pursue a guy that she may have pushed into the friend-zone before since she already knows the attraction is mutual?

I really like this guy I've been friends with for over a year now. We became close while I was going through a divorce so I kept him friend-zoned out of propriety. He's also a confirmed bachelor who likes his freedom but doesn't like being lonely. He's admitted being very attracted to me and being afraid of intimacy. He's like his own worst enemy. He's got the "bad boy, but a good man" thing going on whereas I'm more the "Good girl with an aggressive side". We're both intelligent, independent, passionate, complicated people. I think that's why we seem to connect. We snuggle sometimes and hug for minutes at a time, not letting go and as soon as things heat up, he backs off in this guarded, protective way. I get frustrated because it seems like the only woman he WON'T sleep with is the one he is most attracted to and always talking/texting... the texting often gets sexual which only adds to my frustration. So, I kept my distance for a few weeks. I miss him, though. If he thinks he hurt me, he always sincerely apologizes relatively quickly, as do I. If he thinks I'm mad, though, he keeps his distance. I don't know why. We've fought before and he can hold his own... pretty well, actually.
So, I'm thinking of sending him a point blank text that just says "I'd like to go see a movie with you again." We used to do that together. Is that a level of directness that will more than likely be well-received? Does that cover the bases of "I enjoy your company. I miss you. This is what would make me happy"? Is being direct and initiating things a good idea for me to do in this particular case (even though the guy usually does the chasing)?


Most Helpful Guy

  • Bless the gods, a mate is about to escape the friendzone.

    Well you guys have a long term friendship. At this point I honestly don't think any treading lightly is necessary. I miss you come watch (Movie) with me, should be fine.


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What Guys Said 4

  • If you friendzoned him before he's not going to get the hint if you just ask him to go to a movie, I mean really, it's not rocket science (do you know the story of the boy who cried wolf?)

    Once he gets the hint you have to convince him he's not just a backup for you: tell him that you were attracted to him before and you only friendzoned him because it was appropriate with your divorce and all.

    • Indeed. You're actually not the first to tell me he is afraid of being a rebound or back-up plan.
      I don't rebound. Sex should be about people, not points. Even if I did want a rebound, I would have had it already and I certainly wouldn't make it with someone I wanted to keep around for the long haul. Shouldn't guys be able to tell this about a person... it's not rocket science ;-)

    • How the hell should guys be able to tell that? People lie or hold information back all the time. Women typically lie/hide their sexual past, and that's assuming he feels comfortable asking you about that in the first place.

      When I said "it's not rocket science" I meant that you're going to have to be very aggressive because he's going to interpret any flirting as friendliness since you've friendzoned him before. Every guy knows there are some women who are like that and that the chances of a woman changing her mind about the friendzone are slim so it's not at all unreasonable for him to think like that.

  • If you want him then go after him. Doing things half assed to try and get your point across accomplishes nothing.

  • Be upfront, direct and tell him what you want. Men like an honest and upfront woman with sexual confidence 😉

    You need to shag his brains out @MrsBC95 😉

  • Make it clear that you want him out of your friendzone.