How do I tell him I want to date again?

[laelithia]

Hi everyone,

I'm not sure how to approach this situation. I've been thinking lately about dating my ex again (NOT the one I have written past posts about haha, let's call this one C). We dated for a couple months last year, and I ended it because I didn't think he was attentive enough and he was so independent. He plays a lot of sports and has a lot of friends. Back then, I wanted a "needy" boyfriend so I dated the ex I've written tons of posts about. Bad idea! Anyway, I stayed in contact with C and I would even say we're friends. We have so much in common and I seem to always think about him when I'm with someone else. We have hooked up multiple times since last year so I'm worried that he might not see me in that way anymore. However, he took me to dinner on Sunday and I really felt attracted to him again and we reminisced about old memories. While I was dating my emotionally unstable ex, C tried hard to talk to me about our relationship, saying he wanted a heart to heart and I brushed it off. He would message and call me all the time, and on the weekends often drunk call me, etc. Once he said he thinks I'm the most amazing girl he's met and he messed it up.

 

Now that I'm single again, I really want to give it another shot. How do I go about this now? My friends think I should leave subtle hints that I'm interested so I tried that last night. I told him about how I went speed dating but that I didn't find my dream guy. When he asked why I told him that I already had a crush. He just said "Lol" and asked about the speed dates. Was that a polite rejection? Should I just talk to him and tell him how I feel?

[mhowe]

He didn't get the "hint". Also...he took you out on Sunday and you were texting yesterday. If he were interested, he could have stepped up and said "look no further".

 

He didn't....thus he likely doesn't see you as a potential gf.

 

PS. You can talk to him about it, depending on how well you handle rejection.

[Fame1977]

Just tell him.

 

Start the conversation simple, like... "Hey, remember that "crush" I was talking about"...or something like that.

 

Here's the thing. If you do tell him, you have to go in understanding with he could feel the same or not feel the same. You have to be ready for either result.

[greta96]

I don't think it was a rejection, I think it simply didn't occur to him that after all this time you may have changed your mind.

Your hint was way too subtle lol.

My suggestion is to ask him out to do something you both enjoy doing, and well...act flirtatious and see how he responds to that. You can also ask him, with a playful-flirty smile on your face, how would he feel about giving things another try, now that you're both older and wiser. Be prepared for it to go either way though, and if it doesn't go the way you want it to, for the friendship to be over or become awkward.

[shessofly]

don't hint...just come out with it, but be prepared that he may not feel the same.

 

when you say "hooked up multiple times" are you talking like a fwb situation?

[Clinton]

Hello C, I'd like to try dating again. Simple.

[laelithia]

Thank you everyone for your answers. I'm nervous to tell him for fear that it will mess up the relationship/friendship that we have now. But I think I will casually ask him if he's dating and see what he says. Maybe he's interested in someone else, I have no idea. At least then I can have a better idea where he's at

[laelithia]

Well I did it! I asked him eventually if he liked the way things are between us and he said "I dinno. I don't think I want a relationship, I know that much". So there you have it ladies and gentlemen! I really am taking a break from dating now haha