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Should I message him first?


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Hi, I'm 31, but I look youthful. I've been seeing this 22-year-old for two weeks straight now and for 20+ hours at a time.


Haven't done anything intimate. We finally kissed Wednesday.


I remind him of the fact that I'm 31, but he doesn't care how old I am.


We knew each other from a while back but didn't actually start hanging out until two weeks ago.

The whole reason why I never stay connected with him was because I always knew he was 22, but then when we bumped into each other again we realized how much fun we have together.


He messaged me first again when we randomly bumped into each other, but ever since that first night we reconnected, I've been the one to text him first mostly. He answers me and shows up every time we plan to meet, but it's like if I don't text him now, he won't text me.


For example when I dropped him off Wednesday night, he told me he wanted to hang out tonight.

He said this in person, but if I don't text first, he won't say anything. I watched him.


Last time we said we were going to hang out on Saturday and I waited for him to get back to me and he never did and I met up with him Tuesday to go to our group event together.


We had a nice 2 hour walk on Wednesday and talked about everything and that's when he finally kissed me.


Should I text him first tonight? I'm just tired of texting him first now. I like that he shows up and expresses interest in me in person, but he won't plan the events as if he's waiting for me to plan it.


He was the one that wanted to hang out tonight. I was going to wait until Tuesday to hang out again at our weekly group event, but he doesn't text me to confirm the plan. I feel like he should text me first when he's the one that told me in person he wants to meet tonight.


I never planned on it. We usually hang out during the week.


Should I be bothered that I'm mostly the one who texts him first now after we re-connected? He does express interest in me in person and has even confirmed it by kissing me so I don't understand why he won't text me first to hang out now. Is he intimidated by my age? I can't tell and not sure how I should bring it up.


I'm not expecting anything from him, but I do like hanging out. We like a lot of the same hobbies and foods and this is the first time I've found someone that likes many of the same things I like so it's easy for us to find something to do together and we go to church together. I don't have to force him to go to church he wants to go himself.


I told him I'm not sure about sleeping together also because I don't want it to affect the friendship. That's what we were going to do tonight if we met up and I'm kind of okay with it if he doesn't get back to me but at the same time, it's been a while...Should I wait or say something?


Thanks in advance for any advice.

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Maybe because your older he's waiting for you to take the lead. He's doing what you want to do, when you want to do it. He's more of a follower than a leader.


Maybe he's just going with the flow because you initiate it. When you don't text, neither will he. So to answer your question, no, don't always text first. He has to step up to the plate sometime.

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If he makes the plans then he should confirm a day in advance. If you made the plans you should confirm.


The next time you see him in person ask him straight out. Don't be shy about it simply ask him why he never initiates a conversation or confirms plans that he suggested and waits for you to contact him. See what he says.


Certainly don't sleep with him until you have a better idea where this thing is going. From what you said he sounds like he is in to you when you are right there in front of him but as soon as you are out of sight you are out of his mind. That is not good is it?



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Thanks for the responses guys. I do want to date him that's why I'm not trying to sleep with him right now, but I haven't had any in so long I'm to the breaking point. I've told him up front, too. I'm okay with a fwb, I just don't want it one time, I want it lots of times and he said he wants it lots of times, too, lol.


I texted him right now to confirm if he still wants to meet up today. If I don't hear from him at all for even saying he can't meet up, then I'm not messaging him again.

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I think you'll hear from him.

I'm not trying to sleep with him right now, but I haven't had any in so long I'm to the breaking point. I've told him up front, too. I just don't want it one time, I want it lots of times and he said he wants it lots of times, too, lol.
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I think you'll hear from him.


I hope so. He knows I'm ready and waiting for him to take me to town, haha. Trying not to be too easy. Some friends have told me to play hard to get, too. I just saw him literally a day ago and the day before that so I tell myself it's okay if I don't see him this weekend. We have been hanging out a lot every time we hang out.

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Hmmmm your offering up your body and he really couldn't care less. Do you think he should get the goodies?


When we took a 2 hour walk the other day, he found this private spot and just made out with me when he could have done the whole thing with me. I told him I wasn't going to do anything in a port-a-potty with him, lol. We were on a hike and there were random porta-potties nearby and I said that was gross, lol. I will not do that in there. And he respected my no at the time. A lot of guys I met before him didn't respect me saying no at the time. The other guys thought they could take me out to a nice dinner and have their way with me at the end of the night.



I like that he likes to hang out with me and doesn't expect anything other than a friendship right now even if he pays.



He actually surprises me at 22, he told me he's only been with two people and he looks like the kind of guy who gets around, too.



He never tried anything with me on the first date, either. I think he wants it, too, just at the right time. We have been letting things happen as it happens and not forcing anything. Yeah, I would give it to him. And I told him I just recently got tested and am clean of everything so he doesn't have anything of me to worry about since I'm 31 and he probably figures I've had more experience than him just because I'm a little bit older.


I just hadn't talked to anyone in a long, long, long time before him.


He just messaged me back saying he'll let me know later, whew. Thought the make out session changed the friendship and I was getting worried a bit.

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"If he makes the plans then he should confirm a day in advance. If you made the plans you should confirm.



I disagree. When adults make plans, why call to confirm? What goes on my calendar is what I do. If the woman forgot while I'm at the rendezvous point waiting, then that tells me something very valuable about the woman, and I may or may not give her another chance depending on how things go from there.


Either way, the guy in question doesn't understand attraction unfortunately. As Rambo said up above this post somewhere, he's more of a follower than a leader. That's not what a woman wants in a real man. Not most women, at least. My guess is that if you were to stop texting, he'd text you in maybe a couple weeks. If this guy is a friend, then let me ask you this: Are you always the one to text all of your friends first?


Also, don't fool yourself about the friends thing. You've kissed. You were anticipating the kiss, from the sound of it. You want more than friends, in my opinion. Would you be posting on here if this were just a guy friend? Exactly. So the more important question is not about taking it to the next level and how that will affect the relationship between y'all; it is about whether you really want to take it to the next level with this type of guy who doesn't seem to be a well developed and aware man at this point in his life.

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