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It’s Upto the Woman Sometimes

21 June 2010 3 Comments

I really like this guy I work with. We went from flirting lightly to
flirting alot! He never asked me out though but always makes cute comments
and such. Background on him- he is very family oriented, only has been with
two girls, very shy, columbian and sooo hot! So finally after I give up on
the idea of us becoming anything a day later his cousin calls me (we all
work together) and asks me to go to the pool with the guy I like. They told
me he was too nervous to call me. So we had a blast and kinda did a few
things in the pool lol. He still doesnt ask me out after! A week later, I
hang out with him and his friends at the beach, we all go out to eat and we
play footsie under the table. The next day he finally texts me to hang out.
We go to his sisters and start kissing and stuff but then I had to leave but
he promised this would happen again. I see him at work and he starts talking
to me more and flirting more but he still hasn’t asked me out again. The next
day, we are eating lunch together after we were done working and he randomly
asks if I am into his friend that was at the beach the one day I was with
him. Now I am completely confused. I flirted with him the whole time that
day so why would he ask that! I got kinda mad and didn’t say bye so he
follows after me forcing me to say goodbye to him and I ask if he is trying
to hook me up with his friends? He says don’t be mad it was just a question,
winks and gets in his car. I haven’t texted him nor has he texted me since.
Why would he ask that knowing I obviously like him? So confused and kind of sad
because he is the first guy I have really liked since my last relationship a
year ago. Help please 🙂

Don’t take his comment to heart, he is simply insecure with himself when it comes to women. He asked the question just to make sure that you liked him and weren’t into anyone else. It was strictly out of defense rather than to imply anything. When his cousin told you that the guy you like was too nervous to call you and they had to do it in his place should be enough for you to realize that he does like you, it’s just he doesn’t really know how to act on his feelings.

Take Action

I know women usually dislike taking action and wait for the man to play his part and ask the woman on a date. This time, however, you have stumbled upon a guy who isn’t the most macho man out there, and that’s really alright, you must get comfortable with the idea that he may do things he may not mean or hesitate at moments where he clearly shouldn’t. Though you guys flirt and have made out, he isn’t completely convinced that you want to take things further, therefore he hesitates on asking you out. If you want, the best thing for you to do here would be to ask him if he’s like to meet for drinks sometimes. I know this may sound a little off, but you will have to guide him a little before he can gain enough confidence to know for a fact that you do like him and that there can be a future for the two of you.

Avoid Playing Games

Many times when a man and woman like each other, they end up playing games before they finally hook up. In this case, this man isn’t really used to playing games and definitely doesn’t come off as a player. With him you must approach things differently. Any type of rejection simply to get him to chase you will make him think that he has no chance with you, so it may be best that you avoid playing games with him and be more honest than you tend to be with men. Try being sincere with him when you are on a date and allow him to open up more to you so he can get more comfortable and express himself in a more honest way.

Next time you see him, act like there is nothing wrong and simply try break through his barrier of insecurity and shyness. Lead the conversations, but allow him to get his thoughts out and open up his feelings. This may be a little difficult if you are not used to being the more aggressive person on a date or overall when it comes to dates, but in this case you must be the stronger, more outgoing person to get him to feel less awkward. That includes saying things like, “I expect you to kiss me now” as a joke if you’re in the moment where you feel he should kiss you but doesn’t go for it. Go easy on him while he is still not completely convinced that you like him as much as you really do, and don’t get mad over the inexperiened remarks he may say as he did once in the past.


  • Chloe said:

    You are amazing, thanks so much for your response 🙂 It all makes perfect sense now. I have been giving him the cold shoulder for the past few days because I didn’t know how to really handle the situation. He noticed I haven’t been as flirtatious and asked whats wrong, all I said was ‘you know’ and he completely apologized for the other day and mentioned he didn’t mean it that way. So, you were right! We might have plans for the beach tonight 😉 Thanks again!

  • Robby G (author) said:

    @Chloe: That’s great to hear and I’m sure things will come together as you want them to, because there really isn’t any reason why they shouldn’t. You both like each other and there’s a connection so keep it up and you’ll have a great time. Enjoy!

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