Would definitely appreciate any insights you might have on the following dilemma!
As a bit of background, I’m a man in my late twenties, well educated, confident, and an all round good guy. I never had a whole lot of success with women as a younger man, but now that I I’m all grown up, I’ve been rather successful in courting, dating, and romancing women.
I do however have a very specific and seemingly unorthodox problem.
Conventional wisdom might suggest that expressions of physical intimacy are an indicator of a burgeoning relationship. However, on many occasions the more physically intimate I become with a woman I’m dating (over the course of the first few dates), the more reticence/resistance I encounter on subsequent dates when intimating or initiate intimacy.
If I can distill some of the feedback I’ve received from women, I get the impression that the ladies in question might sense a predictable ending to dates, and/or feel that the date was just a perfunctory prequel to intimacy, and/ or seem to be wanting something “more” on dates (whether that is more face time, more fun, or more of a connection, I don’t know), and/or that I just want to “hook up.”
Given that I am in fact looking for something serious, I’m sure you can see how it might worry me that I give off this impression.
As a bit of context, I usually go for cocktails on the first date and just talk for a few hours. Second date is usually a long dinner followed by a dessert or a good stroll around town (2-3 hours). #3 would be to go to a novel event (a comedy club, art gallery, show, etc., 4-5 hours). Intimacy (not sex) usually occurs on the first or second date and continues thereafter.
Considering the above, I am hoping you can offer some suggestions, and perhaps let me know if I am on the right track with the following thoughts.
- Is the problem simply that the dates we are on are too short in time and are seen only as a prequel? Therefore prolong the dates. Potentially go to multiple venues?
- For later dates (i.e. after the initiation of intimacy), should I plan something more romantic/elaborate? As opposed to dinner or drinks in order to try and change the tenor of the relationship?
- Should I throw in a date where we don’t hookup every once in a while? In other words, does every date have to end with some kind of intimacy in order to stoke a flowering romance
- Should the focus of conversation change from getting to know them in a general sense to a more in depth and personal connection?
I would greatly appreciate any advice!
Thanks in advanced for your time.
LemonVibe 
Something I noticed that you didn’t mention was texting them between dates. You may want to try more talking to them, however it could be you just haven’t found the right woman too and are over thinking it. Best of luck to you!
While men usually need some amount of physical intimacy to develop investment, women are much more likely to get attached to emotional intimacy. If they don’t feel like they’ve gotten to know you on a deep enough level they aren’t going to invest in you long term. They need to see your vulnerability.
Changing things up a bit might help too, pay attention to their personal interests rather than your date night formulas. Some women would find a simple walk in a park or an unconventional date to somewhere unexpected much more romantic than your standard cocktails or dinner date.
But I agree with the previous commenter, communication between dates might help you, let them know you’re thinking about them. But you may have also just not met the right one yet. Don’t sweat it too much. Dating is supposed to be fun. Enjoy yourself, enjoy the company.
I’m extrapolating a bit from your style of writing and the general personality you’re giving off, but here’s my perception of you as a person:
Given how you’ve described the way you plan your dates, you strike me as a meticulous planner. Like, you’re the type of person that schedules everything you do down to the last detail.
Being a planner myself, I think this is awesome … for most aspects of our daily lives. But, I think approaching dating in this manner is ineffective and potentially the reason you’re giving off the wrong vibe to the women you date.
The problem is, women are not tasks that you check off. Every woman you date is different, and every woman is going to want to feel like you’re treating her as a human being, not just some checklist of steps to run through. Because you absolutely are treating your dates in this manner, and whether or not you outwardly reveal this on your dates, I’m guessing you probably project it somehow, and that’s what your dates are picking up on.
Even if you do want a relationship, if your dates get the impression that you expect X to happen on the first date, Y to happen on the second date, and Z to happen on the third date, then they will absolutely believe that you have some sort of ulterior motive or goal in mind.
My suggestion is to try to be more spontaneous. Let a date unfold naturally, and see where it takes you. Don’t be afraid to make decisions on the fly. That’s part of what makes dating fun — and also how you know if you really click with someone.
If you absolutely must plan something out (because hey, I get how that compulsion works), then the way you do so is to have alternate plans. Like, have two or three potential places to go for dinner, have three or four potential activities for afterwards, and so on. And then be ready to decide on one based on how the date is progressing.
Oh, and don’t be afraid to ask for your date’s input on what she would like to you. It’s not just about you, ya know? Dating is a two-way affair.
Basically, don’t date by rote. Because that sounds like what you’re doing right now, and I guarantee it’s going to be a turn-off.
In agreement with the above, dating a guy who’s got a date planned out means hes got the end goal already in mind. Text between dates definitely, try to keep her interest by showing you’re interested in her not just what’s in her pants. Best bet? Stop having sex so quickly. It just furthers the idea of being a casual hookup. Try scheduling friendly get togethers as well, have her meet your friends so she knows that she’s actually got some importance outside of getting laid on the weekend. Do more talking and less drinking on your first date, alcohol is a great way to lower inhibitions but you’re setting yourself up for failure if you spend a whole date just on cocktails. Try setting up a more casual get to know you date with an activity to fill any awkward silences that might happen for a first date. Then use the information from the first date to plan a second date you’ll both enjoy. It’ll show that you’ve been paying attention to her. Try coffee instead of alcohol for going out for drinks if you really wanna do that for a first date.