5 dates and not sure how to proceed

[nychic009]

Hey all, wanted to get your perspective on reading a situation and how I should move forward.

 

 

 

I met a guy around Dec 15. We've been on 5 dates so far, each time with him initiating / asking me out. Here's what our dates look like:

 

 

Date 1: Dinner, he offers to get a car to pick me up, text me after to set up the next date.

 

 

Date 2: Drinks, we talk for 7+ hours, he walks me home, makes out with me in front of my apartment for 20 minutes, tries to put the moves on me, but I didn't invite him in. He asks me out again before he left on his bike home. The mental and physical connection was definitely there.

 

 

Date 3: Dinner, he picks me up, we go back to his place. I can tell he really likes me bc he held my hand and started walking around his apartment showing me his family photos, travel souvenirs, sharing his life with me etc. We start making out and I tell him I don't do casual sex bc of 1) health reasons 2) I'm old fashioned and want him to be my bf first. We end up fooling around but no sex. The chemistry and physical connection was definitely there even though we didn't go all the way.

 

 

This was the night before he left for the holidays and I knew we'd probably not see each other for at least a week. I end up traveling a few days later for the holidays too and while so, he follows up with me, checking in, etc. Here's where it gets weird the 1st time. He asks me how my day was and I answer. I ask him how he was doing. No reply. 3 days pass and I end up sending a flirty message. He messages me back right away saying he was traveling in Aspen. I was REALLY turned off bc 1) he didn't reply to my original message and 2) when he got around responding the 2nd time he didn't apologize for not responding earlier. I didn't respond to that, since I determined he really just didn't care about me that much. I would never not reply to a message from someone I really liked. A few days later, he messages me to see how I am doing and that he missed me. Since I was getting mixed signals, I just played it cool and playful without seeming eager.

 

8 days goes by between that last text until he messages again saying he was finally back in NYC/in town. At this point, we haven't seen each other for 2+ weeks. He asks to see me when I'm free. We end up going on 2 more dates:

 

 

Date 4: We really hit it off again. Conversation just flowed. We were laughing. I could tell we were connecting on a deeper level. I go home with him just to walk his dog together and left early. He messages me when I get home and apologizes for his crazy travel schedule and that he can't wait to see me again. We keep in touch and he asks me out the following week.

 

 

Date 5: He invites me to ballet. He got amazing seats (maybe $300 a ticket?). It was a different date for us bc we've generally have done dinner or drinks where we talked a lot. This was the first date where we didn't have the opportunity to really talk. I offer to pay, he refuses etc.

 

 

After the ballet he wanted me to come back with him. I did and we end up watching a documentary together. We start making out and at some point I asked him a few questions to feel him out like, where he saw himself in 5 years, and his ideal relationship, and so forth. Nothing serious or intense. But I felt like by date 5, I needed to know what he was looking for, without asking too directly.

 

We eventually end up going to his bedroom where I told him again, I don't do casual sex. He said he doesn't either and wants an emotional connection first. I say, I want us to be in a monogamous relationship first (insinuating I don't just want to be sexually exclusive). He said we don't have to have sex today but can just play around. We end up fooling around, no sex, and falling asleep in each other's arms. Next day we both had work early. We walk out together and he calls me a car. Since I was traveling for 10 days after this date, I really wasn't sure when I'd see him or how it'll be when I got back. He walks me to the car and said he'll miss me.

 

Anyway, I end up taking my 10 day trip. Right before the trip, he msgs to wish me safe travels. He checked in right after I landed, during my trip, and wrote me the day I'm back saying welcome home. He has texted he can't wait to see me, he misses me etc. but haven't asked me out again even though we are both in town. I'm pretty confused since as of writing this, it's been a week since I've been back and he hadn't made plans again despite being so thoughtful and sweet while I was away.

 

I *think* I've made it very clear I wanted to see him, bc he had been sick and I offered to come over and make him soup, I told him I missed our conversations, that I wished he was with me on holiday, etc. I essentially dropped hints I wanted to be asked out.

 

Today is Thursday, Valentines day. He last checked in with me Sat night (5 days ago), while I was out with girl friends, and I didn't get back to him until Sun morning. I didn't feel like being so available to a guy who isn't my bf and who didn't ask me out for Sat when I'm actually busy that eve with other people. Plus, it's very normal for him to get back to me in a day, so I'm just mirroring his texting habits.

 

My text Sunday (4 days ago) didn't warrant a response since it wasn't a question but a flirty reply. I'm just confused why he's again dropped off the radar.

 

Should I message again? Is he just trying to avoid Valentines (today)? Why would he be so considerate during my trip and say he can't wait to see me etc and still haven't asked me out? Should I start initiating more? I usually don't initiate until the man asks me to be exclusive but I know for guys maybe he'll think I'm not interested considering I haven't slept with him? On the other hand, I've made it very clear I like him, I just don't do no strings attached sex (and always been this way with every guy).

 

Any advice/thoughts would be appreciated!

 

Oh, I am 30, he is 38. We are both successful professionals in NYC. He is the CEO of a big tv network so I know he is extremely busy. But still, you make time for people you want to make time for. I get that he's probably dating around, as am I. I'm just trying to determine how to move forward with him and get some perspective on what he may be thinking.

Edited February 14, 2019 by nychic009

[salparadise]

I usually don't initiate until the man asks me to be exclusive but I know for guys maybe he'll think I'm not interested considering I haven't slept with him? On the other hand, I've made it very clear I like him, I just don't do no strings attached sex

 

If I went out with someone five times, with no sex and no initiating on her part, and she's saying stuff that indicates that sex is not on the table... I'd probably be moving on. It's not that you're wrong for holding out, but this is 2019 and the old virtuous maiden routine isn't the default anymore. I just don't have the patience to date and date and date without any sex. Most guys are likely to give up after awhile if it's not happening, esp. if they have options. You may have to date a lot of guys to find one who likes being held at arm's length for months.

[nychic009]

If I went out with someone five times, with no sex and no initiating on her part, and she's saying stuff that indicates that sex is not on the table... I'd probably be moving on. It's not that you're wrong for holding out, but this is 2019 and the old virtuous maiden routine isn't the default anymore. I just don't have the patience to date and date and date without any sex. Most guys are likely to give up after awhile if it's not happening, esp. if they have options. You may have to date a lot of guys to find one who likes being held at arm's length for months.

 

 

I get that but I did make comments like "when we do have sex.. " implying if/when we're exclusive that would happen. I guess he just wants to date around? That's why I am holding off on casual sex. I just have no interest in sleeping with a guy no strings attached while he's still trying to date others. It's a huge problem in NYC. And all my gfs who do it never get into relationships and end up getting their hearts broken, on top of being paranoid about STDs.

 

Considering that's the case though, what should I do next? Initiate a date?

[Andy_K]

Time to move on.

 

We eventually end up going to his bedroom where I told him again, I don't do casual sex. He said he doesn't either and wants an emotional connection first. I say, I want us to be in a monogamous relationship first (insinuating I don't just want to be sexually exclusive). He said we don't have to have sex today but can just play around.

 

At this point you've had 5 dates...you say no sex before a relationship. Instead of saying he wants things to move towards a relationship, he counters with 'how about we fool around but don't have sex'. His hope being that either on this occasion or one soon after, you'll be into him enough to drop your rule.

 

He doesn't contact you near valentine's day because that would give out 'relationship' vibes.

 

You're probably not a priority to him at the moment. This might be partly because you haven't had sex with him yet. It might not. Doesn't matter much either way at this point.

[Interstellar]

I’m the complete opposite. I feel that sex clouds the issue and I don’t want to sleep with a woman I’ve only been seeing a few times. Plus, I don’t want my interest level creeping up in the danger zone as I’m less objective if I do that especially if she’s beautiful. Yikes, that would be a recipe for disaster for any man.

 

It’s perfectly acceptable that you don’t want to sleep around living in the city. You have to protect yourself. Absolutely. It’s your body.

 

I think this guy is pulling back because he’s not getting the booty, or his interest is dropping...slowly.

 

Message him? that’s a no for me. Goodbye.

[nychic009]

Time to move on.

 

 

 

At this point you've had 5 dates...you say no sex before a relationship. Instead of saying he wants things to move towards a relationship, he counters with 'how about we fool around but don't have sex'. His hope being that either on this occasion or one soon after, you'll be into him enough to drop your rule.

 

He doesn't contact you near valentine's day because that would give out 'relationship' vibes.

 

You're probably not a priority to him at the moment. This might be partly because you haven't had sex with him yet. It might not. Doesn't matter much either way at this point.

 

 

I agree with your sentiments. I was hoping at 38 he wouldn't be dating just for sex or placing that so high on his priority list.

 

 

 

I'm wondering specifically what I should do, if anything. Should I message him? Or just wait it out/move on? I am going on other dates but felt a stronger connection with this guy.

[Simple Logic]

Considering today is VD I think you will soon have your questions answered.

[ExpatInItaly]

I think he's lost interest, OP.

 

My guess is that he's entertaining other options.

[nychic009]

I think he's lost interest, OP.

 

My guess is that he's entertaining other options.

 

 

Yea, I'm sure he is. We both are attractive successful people with options. I mean, it would be stupid for him not to entertain other options.

 

 

 

I'm just doing what I think is right for me in order to protect myself.

 

 

 

Seems like the consensus is to just leave it alone and NOT message.

[stillafool]

Yeah, single, 38 and the CEO of a large tv network I'll bet there are a lot of women interested in him.

[nychic009]

Yeah, single, 38 and the CEO of a large tv network I'll bet there are a lot of women interested in him.

 

 

Guys, I get ALL of that =). Yes he's very desirable based on superficial qualities.. job, status, looks. But personally for ME, the only things that REALLY matters is his character, how he treats me, and if he wants a commitment eventually. He's a great guy that I highly respect and he has treated me extremely well (with exception of going off the radar for a few days the first time and now). Every time I've spent the night he even kisses me multiple times on the forehead. It's just so cute. I do feel based on our 5 dates, we have a strong connection. He even told me that himself - that our connection is something he hasn't had in a long time. Of course, feelings fade, and he probably did lose interest since I haven't been sleeping with him and he has endless options. I'm okay with that, because no casual sex is a standard I believe in in order to protect myself. If I do have no strings attached sex with him now, not only will he respect me less for dropping my standard, but I'll just one out of many women who is on his rotation sleeping with him. I'll also be opening myself to health risks and getting my heart broken by a guy who is probably entertaining a lot of options.

 

I'm just wondering what I should do next. Should I "chase" him and make a date? Or just let him lead, wait it out/move on and do nothing?

Edited February 14, 2019 by nychic009

[Simple Logic]

Oh yea, I always leave women I am interested in hanging on Feb 14, duh.

[ExpatInItaly]

Yea, I'm sure he is. We both are attractive successful people with options. I mean, it would be stupid for him not to entertain other options.

 

Right. What I mean is that he is probably choosing to prioritize one of those other options over you.

 

I don't think he's as into you as you are into him, OP. Somewhere along the the way, for whatever reason, his head turned away from you. His silence is telling.

[nychic009]

Right. What I mean is that he is probably choosing to prioritize one of those other options over you.

 

I don't think he's as into you as you are into him, OP. Somewhere along the the way, for whatever reason, his head turned away from you. His silence is telling.

 

Yea, I get that sense too. Like I said, when he went off the radar the 1st time, I already determined he took our relationship casually/entertaining a lot of options. You don't not respond to a girls message unless you didn't care/didn't prioritize her at all. When I ignored him/moved on he followed up, probably bc he likes the chase or didn't want to lose me completely.

 

Not sure why he took me out on 2 more dates. Maybe he just wanted to see if I'd have sex with him?

 

Also, not sure why he's making an effort to check in during my trip. I guess he just wants to keep me around as an option. It's not like we're friends and he has to be nice.

 

Keep in mind he initiated and followed up on all 5 dates. I didn't do a thing. So idk, maybe he just wanted to get sex out of me and after the 5th time just gave up.

 

Good thing I am not emotionally invested.

Edited February 14, 2019 by nychic009

[Rockett]

I get why you don't do casual sex, and I think it's very important to protect yourself emotionally and physically. But putting the sex issue aside for a moment, do you think it would help to be a bit more direct with him about what you are looking for? I'm guessing there's a reason that you haven't done this- perhaps the dynamic of the 'dating game' in general, which emphasizes male initiative and female passivity.

 

 

 

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 can imagine going out with someone who eagerly says "yes" to my invitations, but doesn't invite me out. Hard to know exactly where they stand. I wouldn't assume that he knows you are waiting for him to take the lead on moving you both towards a relationship. Personally, I'd want a lot of feedback from the other person telling me that's what they wanted. It would be hard to forge on ahead without that information.

 

 

Still, maybe there is something about him (his success, his options) that makes it hard to approach the "what are you looking for" question directly. If he enjoys the game and needs the "chase," I would be wary of attempting to keep someone like that over the longer term. Perhaps it is best to hold back and observe his behavior- he says he feels a strong connection, but do you feel his actions express that?

[ChatroomHero]

I was hoping at 38 he wouldn't be dating just for sex or placing that so high on his priority list.

 

 

 

He's waited 5 dates and several weeks and probably has no indication of if or when you two will ever have sex. How do you consider that it is high on his priority list based on that? I'd say it is relatively low.

 

 

But make no mistake, for most people sex is one of the most important parts of the relationship. I get not wanting it only to be about sex, but that does not mean sex is not a high priority for most people.

 

 

Sex is the difference between a regular friend and the needs they fill and a SO who fills the needs a regular friend isn't going to. If I were this guy, (not faulting you for your feelings toward the matter), I would get the feeling that if after 6 months and 40 dates we ever did sleep together, it's probably be months before we had sex a 2nd time. I would look at it as you prioritize sex too little. At least that is the feeling I would get, you are traditional and the sex would probably be mild and infrequent.

 

 

Again, your feelings on it are not bad or wrong, but that is the feeling I would get after that many dates and the amount of time that passed.

[Rocker71]

You told him twice in 5 dates that you don't do casual sex.

 

Tbh, I'd have ended it the first time you said it. You may not be this way, but holding out for a relationship and refusing sex for 5 dates, in 2019, could look to him like you're after his resources. Nothing wrong with wanting a relationship, but this is 2019, men today are being taught sex first, relationship possibly later. And that's what the majority of women respond to.

 

Like another poster said, you may have to date and get to know a bunch of guys to find one that wants to go on a lot of sexless dates to get to know you first.

[nychic009]

You told him twice in 5 dates that you don't do casual sex.

 

Tbh, I'd have ended it the first time you said it. You may not be this way, but holding out for a relationship and refusing sex for 5 dates, in 2019, could look to him like you're after his resources. Nothing wrong with wanting a relationship, but this is 2019, men today are being taught sex first, relationship possibly later. And that's what the majority of women respond to.

 

Like another poster said, you may have to date and get to know a bunch of guys to find one that wants to go on a lot of sexless dates to get to know you first.

 

Yea, but then with a guy that has endless options, the other argument is he probably would have lost interest SOONER if I slept with him fast. Instead of 5 dates, maybe he would have faded after the 2nd or 3rd. This happens all the time with men who get a ton of girls.

 

My last boyfriend (who was so hot, every woman would stare when we go out, and quite the catch too) actually told me he doesn't do casual sex and I'd have to be his gf first, and I respected him so much for that. He said he could get any girl he wants. Sex is so easy and that's not a criteria for him to enter into a relationship and if a girl gave it up soon he actually loses interest/respect. I feel the same way.

 

I also don't want to make this all about him. Not to brag but I'm quite the catch too and have no issue finding boyfriends who agree and want exclusivity first.

 

I guess at the end of the day, we just have to do what works for each of us. Play by our own rules.

 

And if/when he messages me again, I should be more assertive about what I want and see what he says.

 

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. Hence I wrote him off until he reached out. And this was when things were REALLY hot and heavy after our 3rd date. Makes me think this guy just doesn't want a GF period, otherwise he would have at least buttered me up when his interest level was at its peak.

Edited February 14, 2019 by nychic009

[Mrs._December]

I get that but I did make comments like "when we do have sex.. " implying if/when we're exclusive that would happen. I guess he just wants to date around? That's why I am holding off on casual sex. I just have no interest in sleeping with a guy no strings attached while he's still trying to date others. It's a huge problem in NYC. And all my gfs who do it never get into relationships and end up getting their hearts broken, on top of being paranoid about STDs.

 

Considering that's the case though, what should I do next? Initiate a date?

You DON'T need to defend your boundaries to anyone. Everyone today seems to think if you're not rolling between the sheets by date 3 then you're not worth their time. Problem is, a lot of these big mouths who hold to the sex by the third date rule are still single. LMAO.

 

So there's that.

 

I'm guessing that when you say you 'fooled around' with this clown, it likely means he got oral sex and was satisfied, and you probably got very little in return. If that's the case, stop doing that. That's so damned one-sided.

 

This guy's been trying to get laid since his second date with you. SECOND date, for crying out loud. Where's the friggen fire? It's very very clear what he's looking for - fun and sex, in that order. He has no desire to couple up with you and be monogamous. He's got a great job, prestige, options galore as far as women are concerned, and he's in his prime, so the last thing he wants to do is have to answer to anyone and be forced to give up his single lifestyle.

 

Ain't happening.

 

I also don't want to make this all about him. Not to brag but I'm quite the catch too and have no issue finding boyfriends who agree and want exclusivity first.

That's perfect! So why aren't you focusing on them, instead of wasting all your time chasing after this playboy?

 

He's a DEAD END.

[40somethingGuy]

Guys, I get ALL of that =). Yes he's very desirable based on superficial qualities.. job, status, looks. But personally for ME, the only things that REALLY matters is his character, how he treats me, and if he wants a commitment eventually. He's a great guy that I highly respect and he has treated me extremely well (with exception of going off the radar for a few days the first time and now). Every time I've spent the night he even kisses me multiple times on the forehead. It's just so cute. I do feel based on our 5 dates, we have a strong connection. He even told me that himself - that our connection is something he hasn't had in a long time. Of course, feelings fade, and he probably did lose interest since I haven't been sleeping with him and he has endless options. I'm okay with that, because no casual sex is a standard I believe in in order to protect myself. If I do have no strings attached sex with him now, not only will he respect me less for dropping my standard, but I'll just one out of many women who is on his rotation sleeping with him. I'll also be opening myself to health risks and getting my heart broken by a guy who is probably entertaining a lot of options.

 

I'm just wondering what I should do next. Should I "chase" him and make a date? Or just let him lead, wait it out/move on and do nothing?

If you feel a strong connection he may too. Maybe instead of playing the mind guessing games, just come out and really let him know you like him and why- connection etc. While you don't have to sleep with him, you could up the ante some and show you are serious if he is. Today is the perfect day for you to take action and let him know you are thinking of him and miss him.

[nychic009]

You DON'T need to defend your boundaries to anyone. Everyone today seems to think if you're not rolling between the sheets by date 3 then you're not worth their time. Problem is, a lot of these big mouths who hold to the sex by the third date rule are still single. LMAO.

 

So there's that.

 

I'm guessing that when you say you 'fooled around' with this clown, it likely means he got oral sex and was satisfied, and you probably got very little in return. If that's the case, stop doing that. That's so damned one-sided.

 

This guy's been trying to get laid since his second date with you. SECOND date, for crying out loud. Where's the friggen fire? It's very very clear what he's looking for - fun and sex, in that order. He has no desire to couple up with you and be monogamous. He's got a great job, prestige, options galore as far as women are concerned, and he's in his prime, so the last thing he wants to do is have to answer to anyone and be forced to give up his single lifestyle.

 

Ain't happening.

 

That's perfect! So why aren't you focusing on them, instead of wasting all your time chasing after this playboy?

 

He's a DEAD END.

 

 

I also got some . He's definitely a giver in the bedroom.

 

 

 

But yea, totally agree with all your points above! I think he was just looking for fun and sex too. The asking me out on 5 dates thing confused me because most men once they find out on date 2-3 they aren't getting laid would have given up by now!

[hippychick3]

I don't think you've done anything wrong here. It sounds like he likes you a lot but not enough to pursue an exclusive relationship. He's not ready to settle down and wants to keep his options open. I would definitely NOT chase him. I'm sure he knows you want him and chasing him will not be attractive. It's Vday and if he doesn't reach out, I'd move on. This guy is just not available for anything other than casual dating/sex.

[nychic009]

If you feel a strong connection he may too. Maybe instead of playing the mind guessing games, just come out and really let him know you like him and why- connection etc. While you don't have to sleep with him, you could up the ante some and show you are serious if he is. Today is the perfect day for you to take action and let him know you are thinking of him and miss him.

 

 

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.

[clia]

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. Hence I wrote him off until he reached out. And this was when things were REALLY hot and heavy after our 3rd date. Makes me think this guy just doesn't want a GF period, otherwise he would have at least buttered me up when his interest level was at its peak.

 

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.

[PRW]

HI asked him a few questions to feel him out like, where he saw himself in 5 years, and his ideal relationship, and so forth. Nothing serious or intense. But I felt like by date 5, I needed to know what he was looking for, without asking too directly

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 was the night before he left for the holidays and I knew we'd probably not see each other for at least a week. I end up traveling a few days later for the holidays too and while so, he follows up with me, checking in, etc. Here's where it gets weird the 1st time. He asks me how my day was and I answer. I ask him how he was doing. No reply. 3 days pass and I end up sending a flirty message. He messages me back right away saying he was traveling in Aspen. I was REALLY turned off bc 1) he didn't reply to my original message and 2) when he got around responding the 2nd time he didn't apologize for not responding earlier. I didn't respond to that, since I determined he really just didn't care about me that much. I would never not reply to a message from someone I really liked. A few days later, he messages me to see how I am doing and that he missed me. Since I was getting mixed signals, I just played it cool and playful without seeming eager.

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.