Had a second date, need some opinions about this guy. (dating, boyfriend)
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So had a second date this past Saturday night, it went really well (I think). The whole date lasted about 7 hours, we went for dinner although had to wait two hours for a table since the place didn't take reservations. But still time flew by because we had great conversation, and we both have a good sense of humor. After dinner we went for drinks, stopped by his house to get his dog (we were in his neighborhood) and went to the bar (the bar allows dogs after a certain time). He asked me about my past relationships and if I ever came close to getting married, and told me about his past relationships as well. He's pretty affectionate towards me without being creepy or pushy, he didn't try anything with me except kissing, at the end of the night we were kissing in front of his house, he asked me if I wanted to come in, I said I better go home (it was almost 3am) he said he understood, asked to see me again, and I said yes (also throughout the night he was making references to when we go out next time). Also during the date I was talking about my mom, and he made a silly joke about her, I jokingly said "I'm going to tell her you said that", and he said "no please don't, because hypothetically if I ever meet her that would be a horrible first impression".
The only thing is his dating rituals are a bit different then what I'm used to. We're from NYC and he's lived in Manhattan for most of his adult life (although he now lives in my borough), I've lived in the outer boroughs my whole life. I'm used to a guy picking me up to take me on a date, however in this case we met at the restaurant, I drove he took an uber. So when we were leaving the place, he knew I had my car (and he lived about a 5-7 minute drive from the place) so I offered to drive him home, when we got in my car I told him this was weird for me since I'm usually not the one driving on a date. He said before the date he was debating whether or not he should call and offer to pick me up (he does have a car btw, but parking in his neighborhood is tough), however he said he was afraid to sound too 1950's and he's used to dating in Manhattan where guys don't pick girls up, they just meet at the place they're going to (which I know is true for the most part). He then went on to say he's not really used to these suburban dating rituals, I told him at where we live is not a suburb, but he said dating here is very different than in the city, but said "I can be taught". The thing is he's almost 40, I feel like some things should just be common sense to a man his age. Also, after our first date which was a Sunday I contacted him first 2 days after the date, but it worked out fine since after that he initiated contact with me for most part and he was the one who asked to see me Saturday night. However I have not heard from him since Saturday, I think I will though, but it bothers me a bit that he doesn't contact me more, I feel like I shouldn't have to wait 3 or 4 days after a date to hear from him, and I really don't want to be the first to contact him after a date again. He's also pretty indecisive, he tends to give me like 5 options on what to do and wants my input, but again in the beginning stages of dating I'm more used to the kind of guy who's more assertive, tells me where we're going and plans the date. All this aside, I have an absolutely amazing time when I'm with him, his personality outshines (thus far from what I know) most of the men I've dated in the past.
I guess I'm just looking for some opinions on how to proceed? Should him not picking me up really bother me? If he does contact me again, is there a way I can hint to him that I'd like him to not wait so long after a date to make contact?
What have you learned about his dating/relationship history? There may be some clues there about his silence or lack of initiative between dates. Or, it could just be that you are one of several people he is seeing and so the next contact isn't as important to him as it is to you. When he asked to see you again, maybe the two of you should have made an actual plan for that next date instead of leaving it so vague. I think that would have been how I would handle it.
I'm not sure how you could successfully hint about it. I would say to just be less available and that may condition him to pick up the pace.
My only experience with dating in NYC is from watching Sex and the City, and I don't recall anyone ever being picked up for a date. Heh. I don't think it would bother me unless it just felt like a total lack of effort or laziness on his part. Thinking it sounds 1950s is just stupid, though.
Possibly suggest you drive one night --he drive the next. Intermingle that with meeting one another somewhere.
This day and age, the man doing all of the driving, picking the girl up seems to be a bit outdated. (Thank you to women's rights--I am grateful these days when a man holds the door open for me and doesn't let it slam in my face.)
As far as the hinting he call you more--really his decision and may come across as being too needy, controlling. Really, if you want to see him, call him. Waiting 3-4 days for him to contact you is not really a long length of time. Perhaps he is doing something else--like working, seeing family members or friends.
You do sound a bit anxious to get more involved with him than you already are and perhaps he is playing it safe and taking his time. Too many people rush into a relationship, giving it their all, making it their priority and then feel devastated if it ends. I suggest you let him make the next move and enjoy your work and other interests. There are some men who may love to be chased by a woman, however it has been my experiences to play the waiting game instead of seeming desperate. It also feels good when I have backed off and leave them wondering about me rather than me consuming so much time wondering about them.
You're in NYC. Are you trying to play hard to get, or just show him how high maintenance you are? Because if you made me drive & pick you up in a town where it is easier to just meet at the destination, I would write you off.
I dunno, it almost sounds like he is over thinking stuff. Most guys I dated would ask if I want to meet or be picked-up, but I think it is considerate he gives you a bunch of options of what do on the date.
The no contact in between would be a turn-off for me, I'm used to guys texting throughout the day. He may be over thinking that too, and not wanting to come off as clingy. Or, you are just not on his mind when you are apart.
Personally, I would sit back an observe how this progresses. Most guys that are into you want to make that clear so you don't start wandering off with another guy.
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I guess I'm just looking for some opinions on how to proceed? Should him not picking me up really bother me?
No. Driving around in Manhattan is a real hassle and parking is super expensive. So why would you want to put him through that nonsense just because you like the ritual of it?
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He's also pretty indecisive, he tends to give me like 5 options on what to do and wants my input, but again in the beginning stages of dating I'm more used to the kind of guy who's more assertive, tells me where we're going and plans the date. All this aside, I have an absolutely amazing time when I'm with him, his personality outshines (thus far from what I know) most of the men I've dated in the past.
He's not a mind-reader and he's just treating you as an equal. And one of the reasons you enjoy his company so much is that he does treat you as an equal and with consideration. He's probably a good listener and not someone who likes to hear the sound of his voice.
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If he does contact me again, is there a way I can hint to him that I'd like him to not wait so long after a date to make contact?
I'd be shocked if he doesn't contact you every again. But you've only gone on two dates and neither of you should be obsessing about this budding relationship yet. He's almost 40 years old and most likely focused on work and the rest of his life. Remember that he's a mature human being with adult responsibilities like a job. And since you are in the NYC area, jobs there are very competitive and demanding. If he was just a burger flipper, then he'd have more time to think about you and text you.
Otherwise, if he was contacting you too soon and often so soon in the dating process, you'd be feeling smothered and turned off by his neediness for you. Yes, you really like him, but don't try to turn this into some great romantic movie plot-line. Instead while you are waiting to hear back from him, do some other interesting things so that you more to talk about the next time you see him.
Relax and take your time in getting to know this guy. Don't chase him. And don't forget to still do things with your friends. It's okay to have him ask you out and you turn him down because you already have other plans. He'll like that you have a life that isn't dependent on having a boyfriend. Remember that he's nearly 40 and not a twenty year old who is more sex-driven.
I'm dating someone now who's long distance (roughly an hour drive) and we somewhat have a schedule now. Pretty much every weekend we'll see each other one day if possible. Our first date was Sunday where she lives and our second date was this past Saturday and she drove here. We have a third date planned for this Thursday pseudo halfway for both of us and our fourth date is Saturday and I'm driving up to her.
I'm not bragging with my statement above, but both of us were very vocal about wanting to see each other again, while we were still on the date. Since we're only seeing each other roughly once a week, we plan for our dates to last at least 4 hours and we stay pretty active during our dates.
This Saturday we drove off the beaten path for bbq, toured a local museum, watched Jurassic World, went a bowled a couple games, and then finished off with dinner at one of her favorite restaurants.
If you like each other, my motto is to always discuss a little of the next date, while you're on your current date. It takes a lot of vagueness out of the situation, and it puts the other person on the spot about actually wanting to see you again. It gives them less time to plan other things in front of you. If you're looking to actually pursue a relationship then you need to lead with your relationship foot. There's nothing wrong with moving slow during the initial period of dating, but 3-4 days of no communication isn't what I call taking things slow either. It's always been non-existent in my book.
What I'm saying is that it doesn't mean the person isn't interested, it just means they may date a different way than what I'm accustomed too. That's where you need to ask your guy what he's looking for. Is he dating around and just enjoying his time or is he looking for the potential of something serious too? I don't mind someone dating around myself, but I know it doesn't fit into the kind of life I'm trying to lead.
It's up to you on deciding what you want. Don't think about being too eager to ask him how he feels about dating. If you don't ask those types of questions, you will never end up in the relationship you deserve.
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