5 dates and not sure how to proceed

[JuneL]

I think this is a huge sign that he doesn't want a girlfriend or anything serious. If you are looking for a relationship, let him go. You absolutely 100% should not reach out to him on Valentine's Day.

 

Regarding the sex thing, you are totally entitled to have your boundaries. I was the same way when I was dating and it definitely helped weed out the guys who were just after sex. That said, I don't understand telling a guy you aren't into casual sex and then getting naked in bed with him and putting your mouths all over each others genitals. Oral sex is still casual sex, so you really are talking out of both sides of your mouth by doing that. It's not a consistent message. He probably expected regular sex soon after you did that.

 

^^^This. I also don’t understand this Bill’s approach to no sex thing.

[nychic009]

This is where it started to go south. You may not think this was too serious or intense but a guy would have. "Where he saw himself in 5 years" is like a job interview question and it absolutely screams "How much money are you going to make for me in the future?" It doesn't matter how YOU meant it,...what matters is how HE is going to take it.

 

I don't recommend you change how you approach on sex. Sticking to your guns is the only way to know if a guy sees things the way you do. If the guy leaves over that then you are better off. So I think you are handling that correctly.

 

This texting drama from both of you is crap. You both need to knock it off. You'll see each other when you get back. Enjoy the break from each other. Look forward to seeing each other afterwards,...and "catch up" then. If I went on a trip, you are only going to hear from me if I have something worth saying. I don't "check in" unless you are my wife or we are in a very solid exclusive relationship.

 

 

I have a very prestigious and successful career too, and come from a lot more than him, so I don't think he should worry about me being a gold digger. I was trying to feel him out if he wanted a family at all, perhaps I should have directly asked that but I didn't want to scare him. This was already 5 dates in and I was not planning to invest anymore time with a guy who didn't have the same future goals as I. I only asked him 3 questions, his future goals, his ideal relationship, and his pet peeves. Is that too intense?

 

 

Perhaps I should have asked these questions sooner. My gfs say I should ask on 2nd date. I don't know. I feel like no one among my friends circle know the correct way to date anymore. I was just enjoying my time with him the first few dates and we were having fun getting to know each other. I did feel awkward asking these 3 questions on the 5th date but it's been a problem in my past relationships where I end up not knowing the mans intentions/goals and wasting a lot of time. He still continued to message while I traveled so hopefully it wasn't as big of a deal.

 

 

Also, he did not mention wanting a family, girlfriend, wife when I asked about his goals in the next few years and I took that to mean again, he wasn't looking for a relationship and definitely not marriage. His parents are divorced and on our first date he told me about how he hated growing up in a house with angry parents. Also, one time the topic of my best friends divorce came up, and the first thing he asked is who is getting the house. All in all I get the sense he has a very negative view on marriage and family and this is not even a priority for him right now even if he did want one eventually. Not sure if I am just convincing myself that and looking for clues, but this all happened.

Edited February 14, 2019 by nychic009

[lurker74]

Sounds like your problem (both of you) is communication. I don't agree that he was avoiding a relationship with you. He showed intense interest and if I were him, I would suspect that you weren't that interested in me. And yet here you are thinking he's not that interested in you. So now you are both ready to walk away because everything isn't perfect.

 

Next time, say to the guy, "Hey...I don't do sex outside of a relationship so let's at least agree to be exclusive with each other for the next couple of weeks and see where it goes..."

 

Otherwise, it's too easy to be taken as, "Nah, I don't want to have sex with you but here's a plausible excuse."

 

In dating, especially in NYC, it's best just to be OK with who you are and state your preference. Some people will not be OK with your preference, which is a great way to weed people out.

[nychic009]

Sounds like your problem (both of you) is communication. I don't agree that he was avoiding a relationship with you. He showed intense interest and if I were him, I would suspect that you weren't that interested in me. And yet here you are thinking he's not that interested in you. So now you are both ready to walk away because everything isn't perfect.

 

Next time, say to the guy, "Hey...I don't do sex outside of a relationship so let's at least agree to be exclusive with each other for the next couple of weeks and see where it goes..."

 

Otherwise, it's too easy to be taken as, "Nah, I don't want to have sex with you but here's a plausible excuse."

 

In dating, especially in NYC, it's best just to be OK with who you are and state your preference. Some people will not be OK with your preference, which is a great way to weed people out.

 

I showed A LOT of interest so he wouldn't think this way.

 

Since I got back from my trip, I've offered to come by and make him soup when he was sick, told him I missed our conversation, said I was thinking about him on my flight, was very flirty with him multiple times when he messaged.. I think he knows I'm interested and want to see him again.

 

Every time he paid for something major (like ballet or expensive dinner) I offered to pay my share, and I brought him little thoughtful gifts just so he knows I'm not using him.

Edited February 14, 2019 by nychic009

[Versacehottie]

I think if you're casually dating a lot of guys go quiet the week and days before--my friends and I have joked about that. Then they will pop back up afterward. I think sometimes they don't know how to deal with the holiday or find it dumb.

 

I think if you do talk to him or go out again you should be less subtle about your interest. Playing it a bit too demure i think. Even if you are fixed on the way you are going to deal with the physical part, you could do some of the initiating texts/calls/dates. I also think it's possible that one reason he likes you is that you are a professional like he is but then in dating you have a more passive style. He could want you two to be a go-getter couple and you haven't exhibit that by asking him to things in your life. That's just a guess. Not all professional guys are like that, of course, but if he's losing interest it'a s possible reason. Goodluck

[nychic009]

I think if you're casually dating a lot of guys go quiet the week and days before--my friends and I have joked about that. Then they will pop back up afterward. I think sometimes they don't know how to deal with the holiday or find it dumb.

 

I think if you do talk to him or go out again you should be less subtle about your interest. Playing it a bit too demure i think. Even if you are fixed on the way you are going to deal with the physical part, you could do some of the initiating texts/calls/dates. I also think it's possible that one reason he likes you is that you are a professional like he is but then in dating you have a more passive style. He could want you two to be a go-getter couple and you haven't exhibit that by asking him to things in your life. That's just a guess. Not all professional guys are like that, of course, but if he's losing interest it'a s possible reason. Goodluck

 

 

Assuming he still contacts me..

 

So I should be less subtle with my interest but continue to not have sex with him? I'm worried he'll totally think I'm not interested then!

 

I used to take charge in relationships (initiating dates, calls, texts, inviting guys to things) but have noticed often it turns guys off bc I'm essentially chasing them. So now, I let the guy lead until he asks me to be exclusive and once we're bf/gf I start initiating.

[stillafool]

Sometimes a man will think a woman is holding out on sex because she wants to appear as 'wife material' and is trying to catch him. I imagine men in his position get this a lot. He seems like a catch so I would imagine a lot of women are using this method to catch him. Not saying you are OP but that is something to think about. Women are afraid if they have sex with a man too soon he will disappear and forget about them. The remedy to this is if you do have sex soon ladies is to make sure you give him something that he can feel not just that night but will linger on his mind. Then give him a lot of space and watch what happens.

[nychic009]

Sometimes a man will think a woman is holding out on sex because she wants to appear as 'wife material' and is trying to catch him. I imagine men in his position get this a lot. He seems like a catch so I would imagine a lot of women are using this method to catch him. Not saying you are OP but that is something to think about. Women are afraid if they have sex with a man too soon he will disappear and forget about them. The remedy to this is if you do have sex soon ladies is to make sure you give him something that he can feel not just that night but will linger on his mind. Then give him a lot of space and watch what happens.

 

 

How I explained it to him and the way I see it personally is that the hook up culture in nyc is rampant. A guy can have sex with 10-20 women in a year and if each of those women is having sex with 10 guys a year I've just slept with 100-200 people in a year. Then the secondary reason is I am just old fashioned.

 

I shower before and after hooking up so he prob knows I'm being honest. I told him I'm a germophobe.

 

I'm not trying to catch a husband this way. Just for my own sanity! I know from my gfs who have no strings attached sex with 2-3 different men A MONTH, then get attached and cry about how these guys don't want anything serious with them. I don't know what's in it for them but I guess this is modern "dating". It's just gross.

Edited February 14, 2019 by nychic009

[stillafool]

I certainly can't blame you for protecting yourself against disease. The guy could be long gone and leaving you with a STD you'll carry the rest of your life. Just not worth it.

[olivetree]

I think that fooling around is not much different than penetrative sex.

If you want to send a clear message that you're serious about not having sex until you're exclusive/in a relationship, then you shouldn't be fooling around at all.

Getting each other off makes it seem like your boundaries are blurry.

 

Anyway, I'd say it sounds like you've made your interest clear and he sees you as a casual prospect.

Not just because he hasn't tried to make v-day plans with you, but because himscommunication has been hot and cold.

 

If he's a CEO, I'm sure he knows how to go after what he wants.

Don't reach out and keep your options open.

[nychic009]

I think that fooling around is not much different than penetrative sex.

If you want to send a clear message that you're serious about not having sex until you're exclusive/in a relationship, then you shouldn't be fooling around at all.

Getting each other off makes it seem like your boundaries are blurry.

 

Anyway, I'd say it sounds like you've made your interest clear and he sees you as a casual prospect.

Not just because he hasn't tried to make v-day plans with you, but because himscommunication has been hot and cold.

 

If he's a CEO, I'm sure he knows how to go after what he wants.

Don't reach out and keep your options open.

 

Yea, I'm definitely not going to chase, will just move on. I doubt he is looking for anything serious right now and I have a feeling had I slept with him sooner he would have lost interest then. It's the connection that makes propels a relationship forward, not rules about when you sleep together, and that connection takes time to develop, not just 1-2 dates so I really don't think I did anything wrong by not sleeping with him after 5 dates.

Edited February 14, 2019 by nychic009

[Juha]

I will guess to say that to him sex is more important in any type of relationship than it is to you.

 

Seems you are mismatched in this aspect and are not a good match.

 

Also, if a woman I liked never initiated anything after a few dates I would feel her interest level was not very high.

 

Dating in NYC can be very difficult with all the people there and so many options.

 

I wish you luck

[nychic009]

I will guess to say that to him sex is more important in any type of relationship than it is to you.

 

Seems you are mismatched in this aspect and are not a good match.

 

Also, if a woman I liked never initiated anything after a few dates I would feel her interest level was not very high.

 

Dating in NYC can be very difficult with all the people there and so many options.

 

I wish you luck

 

 

I don't want to have a FWB relationship, which a no strings attached sex would lead to.

 

I suggested things all the time like "we should do x" and sent him fun flirty / playful messages. I didn't initiate as in I never was like "When are you free?" asking him directly. I think I made my interest clear.

 

He could have at any time asked me to be exclusive but I didn't get he was ready for that (and I wasn't either at 5 dates in, it's a little soon). If he doesn't want to be exclusive I don't think it's unreasonable for me to not have sex with him. It's not like I want to wait till marriage. I fully understand he can and possibly is having sex with multiple women right now and that's not something I want to be a part of. I'm ok just being a friend or moving on/not seeing him anymore. I have no interest in the anxiety that would come with a guy that's sleeping with me and multiple people at the same time.

Edited February 14, 2019 by nychic009

[Juha]

 

I suggested things all the time like "we should do x" and sent him fun flirty / playful messages. I didn't initiate as in I never was like "When are you free?" asking him directly. I think I made my interest clear.

 

You never initiated and asked him out to do something. I would take this as low interest if a woman could never initiate doing things with me.

I have had many women hint around at doing something like you did. Did not mean they were interested or liked me enough to take any initiative.

 

I never said to be a fwb, all I said was sex means less to you than to him in any type of relationship. You are mismatched in this department, which is a big department. He probably takes it that you do not like sex all that much as you only have sex in a relationship.

 

I know lots of people, men and women who will not commit without knowing how the sex will be.

 

I think he does like you, a lot but you won't have sex until tying him down in a relationship. He probably wants to have an idea on what and how sex would be before being exclusive.

 

Also do not think condoms protect you all that much, many std's are transmitted condom or no condom....

 

I wish you luck

[nychic009]

You never initiated and asked him out to do something. I would take this as low interest if a woman could never initiate doing things with me.

I have had many women hint around at doing something like you did. Did not mean they were interested or liked me enough to take any initiative.

 

I never said to be a fwb, all I said was sex means less to you than to him in any type of relationship. You are mismatched in this department, which is a big department. He probably takes it that you do not like sex all that much as you only have sex in a relationship.

 

I know lots of people, men and women who will not commit without knowing how the sex will be.

 

I think he does like you, a lot but you won't have sex until tying him down in a relationship. He probably wants to have an idea on what and how sex would be before being exclusive.

 

Also do not think condoms protect you all that much, many std's are transmitted condom or no condom....

 

I wish you luck

 

 

I do think he likes me a lot, otherwise you wouldn't take a girl out on 5 dates.

 

 

 

I would have initiated to be honest, but the dropping off the radar thing around the holidays after our 3rd date, made me confused. For me to ask a guy out, I'd have to know he's interested in me first, and when he did that I just took it as he didn't care. If he did, he wouldn't have gone cold and ignore my message until I messaged him AGAIN.

 

 

 

I actually was planning to invite him out after I got back from my trip last Thursday. But again, he's MIA around the holidays/valentines. So now, I'm getting mixed signals again and don't feel confident enough to invite him out.

[Versacehottie]

Assuming he still contacts me..

 

So I should be less subtle with my interest but continue to not have sex with him? I'm worried he'll totally think I'm not interested then!

 

I used to take charge in relationships (initiating dates, calls, texts, inviting guys to things) but have noticed often it turns guys off bc I'm essentially chasing them. So now, I let the guy lead until he asks me to be exclusive and once we're bf/gf I start initiating.

 

Sorry if I wasn't clear. Yes I think that you should be more clear that you're into him and have sex when you are ready I guess. Why would showing more interest in him lead him to conclude you are not interested? It should lead him to conclude that you are interested.

 

I agree that chasing guys at the beginning is typically not the way to go. I think 5 dates in you have some traction though and it might be more of a reciprocating feeling or the take charge side of you that initially drew him to you but you are suppressing for dating purposes rather than a chasing him vibe. Right now though because of the pattern, i think you should wait until he contacts you and then within that contact you could be more forward.

 

Another possibility is that i think some women do so make sure you are not, is that they think holding out on sex is the only thing they need to do to keep a guy interested. I think you still have to show him that you are a sexy person even if you aren't having sex yet. I think some women take it way too literal and lose the ACTUAL power that this. (not saying you are doing this i would just make sure that it doesn't apply to you, with him or in the future). I guess i would sum this um as you can probably get away with taking sex of the table immediately but never sexiness. Good luck

[40somethingGuy]

I think it would be desperate to reach out on Valentines. This kind of man needs a challenge and the last thing I should do is let him know I have no plans on V Day and am pining after him. He should be wondering what I'm doing tonight and with who.

 

Although, after this thread, not interested in playing this game anymore. I should focus on other men that's been asking me out.

If you are as you describe yourself- which sounds pretty sexy in our own right- I doubt desperate would come to his mind.

[olivetree]

It's the connection that makes propels a relationship forward, not rules about when you sleep together, and that connection takes time to develop, not just 1-2 dates so I really don't think I did anything wrong by not sleeping with him after 5 dates.

 

Agreed.

I do not give two ****s about rules and sleeping together and whether the guy wants it.

I sleep with someone when I am comfortable, ready and want to.

It's way better when you're emotionally connected anyway.

 

But like I said, I think it's kinda blurry because even though there was no P in the V, you're still having "sex" of some kind in your case.

 

I do think he likes you, but you're not getting what you want / his actions seem casual.

You sound like you have everything together so I think you can find what you want.

[BC1980]

A few things I see here.

 

1. You said no sex until you have a commitment, but you let him sleep over and fooled around. I'm not sure how far it went, but you're sending mixed signals on some level.

 

2. Five dates in two months is too slow to develop a relationship. This indicates to me that he is unserious and probably seeing other women.

 

3. Valentine's Day is a land mine for men. Doing something with you on Valentine's Day would suggest that he is more serious about you than he is. He thinks you might get the wrong idea.

 

4. You've made a wise choice not to have casual sex. Casual sex almost exclusively benefits men. If he wanted to pursue a relationship, he wouldn't be put off by you wanting commitment and monogamy before having sex with him. That's a really basic request if you are looking for a relationship instead of hooking up. You need some more black-and-white boundaries though. For example, allowing a man to sleep over at your house but not having sex is teasing behavior. A clear and realistic standard would be not going any further than kissing until there is commitment.

 

Setting boundaries when it comes to sex is not to play games but to protect yourself. You have figured this out, so you are light years ahead of a lot of other women. I summation, cut bait with this guy, and move on. He's not interested in a relationship with you. Move on to finding someone else. I'm not sure if you want to have kids, but you're 30 years old. Don't waste time that you can't afford.

Edited February 14, 2019 by BC1980

[nychic009]

A few things I see here.

 

1. You said no sex until you have a commitment, but you let him sleep over and fooled around. I'm not sure how far it went, but you're sending mixed signals on some level.

 

2. Five dates in two months is too slow to develop a relationship. This indicates to me that he is unserious and probably seeing other women.

 

3. Valentine's Day is a land mine for men. Doing something with you on Valentine's Day would suggest that he is more serious about you than he is. He thinks you might get the wrong idea.

 

4. You've made a wise choice not to have casual sex. Casual sex almost exclusively benefits men. If he wanted to pursue a relationship, he wouldn't be put off by you wanting commitment and monogamy before having sex with him. That's a really basic request if you are looking for a relationship instead of hooking up. You need some more black-and-white boundaries though. For example, allowing a man to sleep over at your house but not having sex is teasing behavior. A clear and realistic standard would be not going any further than kissing until there is commitment.

 

Setting boundaries when it comes to sex is not to play games but to protect yourself. You have figured this out, so you are light years ahead of a lot of other women. I summation, cut bait with this guy, and move on. He's not interested in a relationship with you. Move on to finding someone else. I'm not sure if you want to have kids, but you're 30 years old. Don't waste time that you can't afford.

 

Thank you. I get the consensous from majority users here “no sex before exclusivity” means I’ll never get a bf bc it’s so rare for a guy to wait for sex past 3/4 dates. This is just not true. I’ve never had a problem getting a serious relationship with quality men in NYC and always held by this standard. You can always break up after if the sex is bad. I even ask both of us to show mutual STD paperwork just for peace of mind. Most men appreciate that. I’ve noticed if anything by holding to this standard men treat me better.

 

Clarifications: I slept over at his bc he insisted (he never came over to mine except outside of my apartment to kiss me). I’m sure I could have left but I had a feeling he would be mad. After ballet for example I offered to go elsewhere for tea (he doesn’t drink at all and I rarely too) but he insisted on me coming over. I wanted to spend more time with him so I said yes.

 

He traveled for 2 weeks for the holidays and travels a lot during the week for work. I also just came back from a 2 week trip and travel frequently for work. So in total we’ve really had 5 dates in a month. But you’re right that the pace is slow, at this stage I would expect things to pick up, not ghost around V Day. I assumed he is going on other dates, as am I. It’s not uncommon in NYC for people to date 3-5 people at the same time for months before making any decisions. It’s a disaster dating here. I find most of my friends who met their partners in NYC and got married were friends / did not jump into a relationship right away.

 

I don’t think I should contact him on V Day. I was the last to reply to his message. It’s his turn. If he wanted to contact me he would have. There’s a reason he’s not.

 

As for initiating more I would usually be initiating more at this stage but like I said, going cold over Xmas/New Years threw me off and again this time. I can’t read him and so I haven’t been taking charge and just letting him show me what he wants. I suppose in a few days I could send a text?

Edited February 14, 2019 by nychic009

[BC1980]

If you replied last, I would let him contact you. You've made it clear you are interested, so it's time for him to reciprocate if he's interested. If someone is interested, it will be clear. There won't be any confusion where you are having to dissect behavior and texting patterns. That's a really good rule of thumb. Definitely don't contact him on Valentine's Day. That's just a land mine of a holiday for anyone who is newly dating.

 

Not having sex until there is a commitment is perfectly reasonable. I've honestly never heard of anyone who stopped dating someone because of this unless the person just wanted sex. I mean, if someone can't wait for a promise of monogamy and exclusivity, that's not the guy for you. The bigger problem I see is the pace and the inconsistent behavior. The fact that he goes off the radar at times does not bode well. It suggests he's not serious and just passing time. He might still be circling around because you slept over at his house, and he's thinking you'd be amenable to sex soon. If it were me, I'd cut bait now. If you want to give it a little longer, no more than a month. It shouldn't take more than 3 months to establish exclusivity. Anything past that, and you're wasting your time.

Edited February 15, 2019 by a LoveShack.org Moderator
quote removed

[nychic009]

It seems like you're holding out for him to ask you out, for him to ask you to be in an exclusive relationship... Do you feel strongly enough about him to tell him that's what you want? Then he can do what he wants with the information. If he feels strongly back, he will act accordingly.

 

I think IF he reappears I can invite him out next time and then have a convo about being exclusive in person. If he says no then go our separate ways.

Edited February 15, 2019 by a LoveShack.org Moderator
edited quote

[greymatter]

Seems like you believe you are "old fashioned" because you "held out" and didn't have penetrative sex. But it sounds like you gave each other oral sex which some consider to be even more intimate than what you consider to be "sex." To a lot of us, sex is sex at that point. If you went as far as oral sex, you two had sex. It also is risky from an STD standpoint (for herpes, not a dangerous STD but no fun to have for a lifetime, I'm sure).

 

I'd be interested to know why oral sex doesn't equal sex to you, but penetrative sex does?

 

You having a narrow/rigid definition in your mind of what constitutes sex doesn't change that you did have sex with him. It is possible that he experienced that as frustrating, unsophisticated, and not very mature of you -- to go as far as you did and refuse to do more, not because you weren't into him, but because you wanted him to commit to more after just a few dates before you would "go all the way" and because you care more about coming off as "old fashioned" than actually communicating what you want and letting things sort themselves out based on his response.

 

I don't think he is all that interested, given the slow trajectory of your dates and minimal communication. You seem very stuck and to have rigidity around sex and "what is proper" by your own definitions, and may be getting in your own way with that. It just doesn't sound like you holding out for intercourse caused things to build in the way that you were hoping for, which is disappointing I'm sure.

[GraceAndJoy]

Oh, and isn't it weird that around major holidays he always goes MIA? The first time he went off the radar around the holidays I also never got a Merry Xmas or Happy NY from him.

 

This is a huge red flag that he could already have a girlfriend/special someone. When a man has a "side piece," the primary piece always gets the holidays (Christmas, New Year's, Valentine's Day). He could be seeing you when she's out of town or unavailable.

 

Sorry, OP, but in my experience, if a guy is really into you and wants to build something with you, you will be on his mind on special days/travel days.

[nychic009]

Seems like you believe you are "old fashioned" because you "held out" and didn't have penetrative sex. But it sounds like you gave each other oral sex which some consider to be even more intimate than what you consider to be "sex." To a lot of us, sex is sex at that point. If you went as far as oral sex, you two had sex. It also is risky from an STD standpoint (for herpes, not a dangerous STD but no fun to have for a lifetime, I'm sure).

 

I'd be interested to know why oral sex doesn't equal sex to you, but penetrative sex does?

 

You having a narrow/rigid definition in your mind of what constitutes sex doesn't change that you did have sex with him. It is possible that he experienced that as frustrating, unsophisticated, and not very mature of you -- to go as far as you did and refuse to do more, not because you weren't into him, but because you wanted him to commit to more after just a few dates before you would "go all the way" and because you care more about coming off as "old fashioned" than actually communicating what you want and letting things sort themselves out based on his response.

 

I don't think he is all that interested, given the slow trajectory of your dates and minimal communication. You seem very stuck and to have rigidity around sex and "what is proper" by your own definitions, and may be getting in your own way with that. It just doesn't sound like you holding out for intercourse caused things to build in the way that you were hoping for, which is disappointing I'm sure.

 

I’m not interested in coming across old fashioned. I just am scared of diseases and I don’t want to invest emotionally while he’s potentially sleeping with others.

I wasn’t using sex as a means to get him to commit. It’s my own standard for protecting my health and my heart. I get that many guys want sex before exclusivity / casual sex I guess those are the guys that I can’t date bc we have different values. If that makes it harder for me to find a guy, I’m willing to face those consequences.