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Where do I stand with this guy? 6 dates - Still can't read him


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Posted

So I've been seeing this guy I met online for 6 weeks now (I wrote about our 1st three dates in my last thread) -- and I'm SO confused on where this is -- or isn't -- going. Here are the main details:

 

-Both in our mid-late 30s.

 

-Our 1st date was technically six weeks ago; but he's been away on two week-long trips since then, and I've been on one -- so we've only been in town at the same time for 3 weeks over the course of that time. In that time we've been on 6 dates--all initiated by him, and all secured well in advance (like 4-9 days ahead of time, which seems really considerate of him). The dates themselves definitely don't feel like booty calls -- we've gone to nice restaurants, he always wants to pay (although i've hijacked the check twice), and he seems very "respectful" and not overtly focused on sex.

 

-On our second date, when we first fooled around, and he wound up sleeping over, he seemed very open/complimentary/affectionate...maybe a little more aggressive (note: we both drank more on that date than on the others). Due to our travel schedules, it's also been our only weekend date. All the dates since then have also been sleepovers.

 

-Dates 3 & 4 that felt awkward by comparison. We are definitely both on the shy/polite/reserved side...and this definitely seemed evident in our physical interactions and conversations on dates 3 & 4. I also got *really* nervous before both of these dates, which didn't help. Each time, when we'd (awkwardly!) say goodbye in the morning, I'd secretly feel sad and worry he didn't like me anymore. Yet he'd always text/chat me a bit later in the day to check in, and then I'd think "oh, maybe i was worrying over nothing."

 

-Dates 5 & 6 def felt better in terms of awkwardness on the dates themselves. But there's still this kind of intense reserve that I can't get past. Like we'll meet each other and like I kiss him on the cheek (not sure what I'm supposed to do!), and then we'll have a totally nice dinner, usu with pretty but very polite good conversation and sometimes a movie too. He's very like "gentlemanly" but a little passive. Then he'll either walk me home (and i invite him up) or he invites me over. And then we watch tv or movies -- either awkwardly or cuddling (which is super nice, but the initiation, again, is awkward). Only AFTER that will we make out/sleep together/whatever. Also, other than Date 2 he doesn't exactly flirt with me -- and he hasn't, like, "complimented" me. Which is a little weird....

 

-Keep in mind that all of these are broken up by one or the other of us traveling. Which breaks up the momentum a little and may or may not be contributing to the awkwardness.

 

-He initiates pretty much 100% of our texts and online chats -- but they're not particularly engaging. More like checking in. Which is sweet -- but I'm never sure how engaging to be in my response. I feel like I often kind of just leave the exchanges hanging bc I don't know what to say. He's initiated texts also when either he or I travel...also nice. But very kind of "neutral" texts

 

-The thing that is confusing me/upsetting me MOST is this: After we have sex, he's usu pretty chatty. Which I like. It's sweet. BUT...when we're finally ready to go to sleep (usu v late) he DOESNT cuddle w me. I think he did our 1st 2 sleepovers but not since then. Maybe our legs our touching....but it's like NO cuddling. EVEN worse is waking up in the morning. I go to work earlier than he does. My alarm usu goes off ... i snooze a few times. Of course he hears it too. I always want him to turn over and kind of be affectionate at that time but he's blatantly NOT. He'll like be looking at his phone or turned away... there's nothing! Eventually I just jump up and run to the shower and spend the next 30 mins getting ready. By the time I come out of bathroom he's dressed, politely sitting on my couch waiting for me. He walks me to get coffee and then to the subway and during this time he'll usu ask about my schedule and talk about when we can hang out again next. I awkwardly kiss him on the cheek, say goodbye. Then, like I said, he usu texts or chats a few hours later just to kinda check in.

 

Anyway, not sure if I'm over thinking this or what! But I have NO clue what's going on here. I don't know how affectionate to be or not be. I don't know if he's obviously keeping some kind of distance or just being shy/awkward. Not sure if I should start initiating stuff too, or continue to let him lead. In case you can't tell, I feel like I could really like this guy.

 

Oh, one more thing. I KNOW that I come across as shy/awkward/hard to read. I'm def used to being with men who are a little more alpha/open/aggressive than this guy is, and with them my shyness isn't such of an issue (though they always mention it later). This guy has said he's shy/introverted. But he's also, objectively, a *really* good looking/smart guy....I have a hard time believing he doesn't know how to navigate stuff with girls.

Posted

Stop sleeping with him, and only give him affection if you feel like being affectionate, and not as a way to try to get him to be affectionate back. Observe how he behaves, and go from there.

  • Author
Posted

Treasa,

 

Hmm, thank you for your response. Just to clarify: Actually, I haven't been affectionate. As I noted, I'm pretty reserved/shy and if anything my confusion here is making me even more so. That being said I'm definitely "nice" -- and so is he... I dunno...

 

Regarding the suggestion to stop sleeping with him -- are you saying this because you think he's using me for sex? I *really* can't tell. I'm not convinced he'd bother being so considerate, booking ahead, taking me on nice dates, etc. if all he wanted was sex (a guy with his looks in my city could EASILY get sex without all that hassle). Still, I'm not completely confident about this -- and I remain open to your suggestion. I guess I'm also not sure how I'd actually go about it, and if it would really have the desired effect. Would I suddenly say, oh btw I don't think we should sleep together anymore? I imagine this would come across as me being calculating and game-playing.

 

Thoughts appreciated.

Posted

I may have misread that HE was the shy/reserved one.

 

I'm not suggesting that he's using you for sex, just that you may not want to sleep with him if it makes you feel bad, until you know where you two are.

 

Unless you're ok with just having sex, which is fine. ;)

 

You can't make someone affectionate, so chances are you're seeing who he is. You can try being affectionate, but if he doesn't return it, then you'll know.

  • Like 1
Posted

I think it's awkward because you guys don't even know each other yet all you've done is jump to sex. Of course it's going to be awkward with a person you barely know!

 

You need the foundation... the emotional foundation, the friendship foundation... I mean yeah it's cool, you're obviously attracted to each other but neither of you really knows the other. Why not spend time OUTSIDE of the bedroom? DO things together. Find out what your hobbies are, what kind of personalities you both have (on a deeper level than what you're doing now.)

Posted

I don't get the impression that he's using you for sex, but it definitely is strange. It's like it's just a casual hanging out for companionship when you're both available, kind of thing. You are both very passive, both afraid to be the one to take it to the next level.

 

I feel kind of like he thinks he's giving you a lot of signs and wants you to move things along. Like when your alarm goes off in the morning, why just lie there and wait for him? Start touching him.

  • Like 3
Posted

Not everyone is overtly physically affectionate. Not everyone wants to cuddle when they sleep. Some people are naturally more reserved than others. It doesn't necessarily reflect the depth of their feelings.

 

From everything you describe, it sounds as if he is definitely interested in you. If you want playtime in the morning, then it's okay for you to initiate. If you want to be cuddled, then tell him. Perhaps he gets hot and can't really fall sleep while cuddling with someone. Who knows? You have to communicate and compromise where needed.

 

Anyway, worry a little less. Relax. Go with the flow. He sounds sweet and considerate overall.:)

  • Like 2
Posted

He's probably just as unsure about this as you are. As a man it can be very exhausting being the one to initiate Every. Single. Thing. The fact that you don't initiate text messages or any other type of affection is probably very frustrating to him. Send him a message out of the blue just to say hi or ask him how is day is, I bet he'd love it.

  • Like 2
Posted

I think you need to put forth a little more effort. It sounds like everything is on this guys terms, for example "he is casual in our chats so I don't know how engaging to be"....be as engaging as you want! Why is it dependent on him? maybe he feels awkward cause you just sit back and wait for him to do all the work. He probably has no idea if you truly even like him if he has to initiate 100% of dates/conversations 100% of the time!

 

Also you need to incorporate more casual/fun dates. Not just dinner. Do an activity together, it will help you bond rather than just convo over dinner.

  • Like 2
Posted

It sounds like you jumped to one level of intimacy pretty quickly, but your respective personalities have trouble with it on a real level. If you're naturally affectionate, playful etc and you have sex pretty quick it's fine because it becomes an extension of the relationship as a whole. If either or both or you are more reserved, then sex can possibly create more awkwardness, because you haven't built up the comfort level in other aspects of the relationship.

 

How IS the sex?

 

I would try and have at least a couple of dates without a sleepover. And maybe forego the sex too. Find an innocuous excuse to make a date end earlier than it might normally. And just try to have fun that way.

 

I agree, too, with the comments above that you should reciprocate signs of interest.

  • Like 1
Posted

The thing that jumped out at me was that he cuddled first couple of times and stopped. Indicates to me he can't tell if you liked it. Need to be more responsive to him (with your body and words). Awkward to start cuddling on couch? All you two have to do is lean on each other. How hard is that?

 

Also cuddle up to him when going to sleep. If that bothers his sleep and he says something that's something else, but would be surprised at a guy that doesn't like that (and very appreciative).

 

Also cuddle and kiss more before having sex. Get a little more passion going, ok a lot more.

  • Like 3
Posted

Let me blab about my experiences for a bit.

 

I'm pretty traditional about the early stages of dating, I think. I want the guy to ask me out, to plan the dates, to make the moves, etc. BUT - once we've reached a particular milestone or whatever you want to call it, I have nooooo problem initiating that later on. For example, I won't initiate a first kiss. But once we've kissed - I'm going for it when I want it! If I want to cuddle - I just do it. If I want to hold hands, I don't walk along wishing he'd take my hand. I take his. Now - if I'm ALWAYS the one initiating, then I might get annoyed... but chances are that things would have died off for other reasons before it got to that point.

 

If he didn't want to be there, he wouldn't be there. Don't be shy.

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