Dear Ms. HeartBeat:
A few months back my guy friend started messenging me and calling me a lot, to the point where we were hanging out every other day. We spent several holidays hanging out together as well. All my friends said that he was into more than just being friends, and one of my friends even asked him, but he replied that we were just friends.
Later on he texted me to say he didn't think he would do anything to ruin our friendship, which i was completely fine with cause I wasn't sure if I liked him romantically anyway - it was more my friends thinking he was into me that way.
Anyways, we continued to hang out; he would come over watch movies, cook dinner, go out to drink, and while we were drinking one night he got touchy with me. He touched my hand one night in the car, my leg on another evening, and I was like this feels like he likes me, but why revisit the conversation or thought again?
So eventually I stopped calling to put distance between us because I ended up liking the attention he was giving me. In other words, here I am at 33 falling for my 36 year old guy friend. I wanted to protect my heart, so now I see him just once a week, and he contacts me via text or on Facebook.
I'm writing you because the other night we went out for drinks (he paid), and he asked me if I wanted to go on a vacation to some tropical place which he sent me flight rates for. Now I'm confused again. Is this what it's like for a guy to lead you on? Do you think he's just lonely?
I really don't want to bring this conversation up again, but now that I finally think I like this guy, how stupid would I look to bring it up again? I'm lost, I know it seems simple to people like you, but for me this is a gamble. I could be wrong and lose him as a friend. What should I do?
Slow But Getting There
You need to be direct and ask him "why are you asking me to go to some romantic place with you, just the two of us, if we are not involved? That sounds like a boyfriend/girlfriend trip, not a platonic friends trip. What is it you are really asking me here?"
Since the two of you are old enough to "hang out" in bars drinking, that means you're not a child. As a woman, you must take the initiative to make sure that you understand what it is other people in your life expect of you. Just as you'd ask for clarification from an employer before taking on an assignment or accepting a job, you should do the same here.
He has already told you that he is terrified that he'll do or say something to ruin the friendship, which you accepted because you weren't really into him 'like that' months ago. However, by being around this young man you've grown to care for him because you were allowed to see who he truly is without the complications of sexual interaction. This is the ideal start to a long-term relationship because you really understand who it is you'd be involved with... no rose colored glasses.
Take the bull by the horns, chicka. Stop allowing him to beat around the bush. Be honest about your feelings of confusion and ask him directly what it is he wants. Touching all over you while saying he doesn't want to mess up the friendship is sending a very mixed message, and you need to let him know that. You are plenty old enough to open your mouth and demand clarity from a man!
Then tell him what you want; he can either say "yes I want that too but I was scared you'd be angry!" Or he can say "no, I just wanted to get laid and thought since we are already friends we could be friends with benefits."
But there is no reason for a 33-year-old woman to behave so timidly with a man. Get it out on the table. As fabulous as I am, even I cannot see into the future or read minds. I can't tell you what he is thinking or feeling - that has to come from HIM.