Does he want me to initiate? Or does he only like me as a friend?

[bubumon]

A few years ago I met this guy and he knew that I liked him (I sent obvious signals, asking him to dinner, flirting, etc), but he never initiated so I went out with another guy.

 

Over the years the guy and I continued to keep in touch - I ended up breaking up with my then boyfriend, he went out with another girl and broke up. We meet for dinner and hang out every so often, and a couple of years ago I asked him, "Did you know that I used to like you?" to which he said, "Yeah, I knew", and left it at that.

 

He continues to text me every few days (he usually initiates the texts) and recently asked me to go on holiday with him. I told him sure, but he hasn't given me a date of when he can go when I followed up.

 

I do get a vibe from him that he likes me, but every time we go hang out, we talk and laugh and have a great conversation, but he never makes any moves on me. Knowing that he knows I used to like him, I don't try to make it obvious (or hide the fact that I like him) - I just act myself around him.

 

With texting being our main form of communication, should I be more flirtatious to make my message clear? (Stuff like, "I'm thinking about you" - i.e. stuff I never say to him usually) Or should I just take it as a message since these past few years he hasn't made any moves on me that he only wants to be friends? (But on the other hand, I don't have any other platonic male friends asking me to go on holidays alone with them, or texting me every other day...)

 

Please help! Any suggestions/insights are highly appreciated, thanks!

[Sw3etdev1L]

When I was 17 I used to have this huge crush.. he was shy, I was shy... everytime I saw him my heart felt like it was about to burst, I used to get all blushed and sweaty and, I thought I couldn't even talk to him because I liked him so much. Everytime he would try to talk to me he would smile and try to talk but couldn't.. time passed, years passed... and we became msn friends, that's the media with which we overcame shyness, and saw each other as we grew up... then we became friends, and yes we did kiss and we did cuddle a little...

Nowadays that relationship is over, I have my boyfriend which with I am thinking of marrying and having children with and my teenage crush faded away.

Teenage crushes are gold when you make them come true I believe.. At least try. After my friend and I talked we both said.. if we both have not been shy in highschool maybe something would've happened and our story couldve have been different.

I really thought that after two years of kknowing him we would get married. I liked him, we were compatible and, our relationship was great.

What I am trying to say is... Leave your feelings aside (fear,anxiety, shyness, supossitions), and just ask to yourself.. ¿what is it that I want to live in the now?... life changes so much, and ¿what if in this moment you could live a relationship , a real relationship with this person?... if he doesn¿t make the move, you can do it... I am not saying, " go ahead and be slutty, or needy", but.... you could risk it and give him a letter, he is your friend after all right?... You could be suggestive in a non aggresive way, by writing him a letter saying that you would want to be something more than friends with him.... ¿what if he likes you too? you could have a great time in your life if you both turn out to like each other.

[SpiralOut]

If he wanted you as more than a friend, he probably would have made a move on you by now. Maybe he thinks that you no longer have feelings for him. Right now I am thinking that he either a) likes you as just a friend, or b) doesn't know what he wants.

 

How is he with his other female friends? Does he go on trips with them too, or is he like this with just you? Does he text his other female friends?

 

Personally, I would go the direct route and just straight up ask him.

[NoMagicBullet]

I agree with SpiralOut, although I'd add that being confused means lack of sufficient interest anyway. The only way to know for sure is to ask him. You let him know how you felt in the past, and even when you were both available, he's never made a move. He's had plenty of opportunity and he knows the risk of rejection with you is low. I'm sorry, but if he was interested in dating you, he'd have asked you on real dates by now.

 

To me, the invitation to go on holiday sounds like he either a) wants to keep things platonic and just wants a friend along, or b) he's considering a holiday fling with you and nothing more. So I don't think you should try being flirty, because combining your flirtation with his invitation may be interpreted that you're open to a holiday fling or perhaps a FWB arrangement. Unless either of those are what you want. However, if you've liked him for so long, I don't think you'll be happy with either of those situations in the long term.

 

Since he's a long time friend, maybe you two could sit down and really discuss what sort of relationship each of you would like to have in the future: platonic friends or something more, and what type of "more" if so. If you get vague or unclear answers from him, he's likely not feeling the desire to make you his girlfriend -- then keep things platonic so you don't get burned.

[bubumon]

Thx for your responses - I'm not sure whether he texts his other female friends on a frequent basis, but I do know that he doesn't go on holiday with girls alone, aside from going on holiday with his ex-girlfriend.

 

On the other hand, he knows I've been on holiday with a guy (alone) before and was confused about why that particular guy didn't make a move on me while on holiday....so I'd assume he would know that I expect a guy who asks me to go on holiday with him would be interested in me...