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After taking a dating hiatus, I jumped back into online dating a couple of weeks ago. And have had interesting dates and good ones.
Overall dating intentions are to have fun, meet the right person, and find a long term person. So I have been open to meeting people and seeing where it goes as long as directionally intentions are similar.
And the two most recent people are opening up some interesting questions for me. I've got nicknames for them to make it simple:
Mr. Easy and Mr. Challenging
I have a basic archetype: generally if I am going to put a label on it I like bald men with great smiles who are social, confident nerds with swag. I can be flexible on the swag. Bonus points if you are stylish, but at the minimum you have to clean up nicely.
Mr. Easy
I've been talking to Mr. Easy for a little over a month, we have had 3 in-person dates. The 4th got postponed to this week because he was sick. During this time we have texted daily (sometimes flirty), but also have had opposing schedules. He has partial custody of a kid and I had some traveling. His goals are companionship, seeing where it goes, and potentially long term.
Date one started with drinks that went well so we had dinner. Date two was drinks and dessert at a bar. Date 3 I invited him over for a tequila tasting (only tequila tasting, not more physical intimacy). We've done a bit of drinking, but neither of us has a high tolerance 1-2 drinks and we are done - so it was social drinking not for loosening up purposes.
What works: lots of common interests, similar world view, decent romantic chemistry, easy conversations. We like to do the most of the same sorts of things in free time. We like the same sorts of travel destinations/activities. He's totally fine with me having higher income potential. We haven't broached any super deep topics yet, but all in all a good fit. He's separated, we talked about if he wants more kids or wants to get married again.... a few things like that. He fits easily in my life as is! He is an easy going guy - he's not going to lead me down any new paths (except for trying to make me eat mayo lol or do more high brow cultural stuff). He is basically a clone of most of my friends.
Dates with him have been fun and frothy I guess. Lots of talking and laughing!
Meeting him for date 4 this week, maybe it is deeper topic time. I am supposed to go to his home for dinner!
Mr. Challenging
I connected with Mr. Challenging a couple of weeks ago on Bumble - great initial convo he responded perfectly to my weird opener. He seemed to be pretty busy and was slow to respond. We moved to text convo. Mr. Challenging is goal oriented (and overcame some life challenges) and he is absolutely ready to settle down into a long term monogamous relationship. But also mentioned he likes to wait for an emotional connection before having sex. He skipped most of the small talk and jumped into the deep questions (there was still some joking, it was not all serious convo):
- what does being in love look like for you
- what do you want your next relationship to look like
- being emotionally vulnerable
- what's sexual intimacy for you (this can be a red flag question if it happens to early, but I assume anyone who leads with I am waiting is probably not asking because they want a hookup)
After a bit of back and forth and good phone call, we made tentative plans that didn't happen. The vibe I got from him is that he prefers leading and pursuing, so I didn't reschedule. But after a few days of quiet, he reached out and we ended up making some last minute plans to meet over the past weekend.
I met him for drinks that turned into dinner and a walk, so we had a good few hours together. It was a good first date. More interesting questions. Easy conversation through out the date. He is a bit intense, but did laugh. Based on the convos to date - reasonable amount of common interests. He seems pretty go with the flow on that respect. We didn't talk super deep about those things, but seemed amenable to my suggestions and the things I usually do. And did not judge me for consuming terrible pop culture media!
So what makes Mr. Challenging a challenge? So many of the questions he asked me were things I had never spent time thinking about and certainly haven't articulated. So this made us connect on a deeper intellectual level! One of the things on my "list" is having a partner that can push me out of my comfort zone and this person was able to do that in early conversations and a first date.
Also I am known for being both friendly and also unreadable. I am really easy to get along with, but it takes generally a bit of time to get to the core me. I was shocked that he actually got a pretty good read on me in a first meeting. That never happens. So this was a super interesting and new experience for me. I left the date feeling intrigued.
So we'll see, he wanted to setup a second date and asked for suggestions. I said yes and he has the ball, so It is up to him to schedule. We did text a bit over the rest of the weekend, more deep topics.
Anyway it is weird to meet people that are kinda similar and wildly different at same time. I think at a different point in my life, Mr. Easy would be a no-brainer. Now I am not so sure.
After taking a dating hiatus, I jumped back into online dating a couple of weeks ago. And have had interesting dates and good ones.
Overall dating intentions are to have fun, meet the right person, and find a long term person. So I have been open to meeting people and seeing where it goes as long as directionally intentions are similar.
And the two most recent people are opening up some interesting questions for me. I've got nicknames for them to make it simple:
Mr. Easy and Mr. Challenging
I have a basic archetype: generally if I am going to put a label on it I like bald men with great smiles who are social, confident nerds with swag. I can be flexible on the swag. Bonus points if you are stylish, but at the minimum you have to clean up nicely.
Mr. Easy
I've been talking to Mr. Easy for a little over a month, we have had 3 in-person dates. The 4th got postponed to this week because he was sick. During this time we have texted daily (sometimes flirty), but also have had opposing schedules. He has partial custody of a kid and I had some traveling. His goals are companionship, seeing where it goes, and potentially long term.
Date one started with drinks that went well so we had dinner. Date two was drinks and dessert at a bar. Date 3 I invited him over for a tequila tasting (only tequila tasting, not more physical intimacy). We've done a bit of drinking, but neither of us has a high tolerance 1-2 drinks and we are done - so it was social drinking not for loosening up purposes.
What works: lots of common interests, similar world view, decent romantic chemistry, easy conversations. We like to do the most of the same sorts of things in free time. We like the same sorts of travel destinations/activities. He's totally fine with me having higher income potential. We haven't broached any super deep topics yet, but all in all a good fit. He's separated, we talked about if he wants more kids or wants to get married again.... a few things like that. He fits easily in my life as is! He is an easy going guy - he's not going to lead me down any new paths (except for trying to make me eat mayo lol or do more high brow cultural stuff). He is basically a clone of most of my friends.
Dates with him have been fun and frothy I guess. Lots of talking and laughing!
Meeting him for date 4 this week, maybe it is deeper topic time. I am supposed to go to his home for dinner!
Mr. Challenging
I connected with Mr. Challenging a couple of weeks ago on Bumble - great initial convo he responded perfectly to my weird opener. He seemed to be pretty busy and was slow to respond. We moved to text convo. Mr. Challenging is goal oriented (and overcame some life challenges) and he is absolutely ready to settle down into a long term monogamous relationship. But also mentioned he likes to wait for an emotional connection before having sex. He skipped most of the small talk and jumped into the deep questions (there was still some joking, it was not all serious convo):
- what does being in love look like for you
- what do you want your next relationship to look like
- being emotionally vulnerable
- what's sexual intimacy for you (this can be a red flag question if it happens to early, but I assume anyone who leads with I am waiting is probably not asking because they want a hookup)
After a bit of back and forth and good phone call, we made tentative plans that didn't happen. The vibe I got from him is that he prefers leading and pursuing, so I didn't reschedule. But after a few days of quiet, he reached out and we ended up making some last minute plans to meet over the past weekend.
I met him for drinks that turned into dinner and a walk, so we had a good few hours together. It was a good first date. More interesting questions. Easy conversation through out the date. He is a bit intense, but did laugh. Based on the convos to date - reasonable amount of common interests. He seems pretty go with the flow on that respect. We didn't talk super deep about those things, but seemed amenable to my suggestions and the things I usually do. And did not judge me for consuming terrible pop culture media!
So what makes Mr. Challenging a challenge? So many of the questions he asked me were things I had never spent time thinking about and certainly haven't articulated. So this made us connect on a deeper intellectual level! One of the things on my "list" is having a partner that can push me out of my comfort zone and this person was able to do that in early conversations and a first date.
Also I am known for being both friendly and also unreadable. I am really easy to get along with, but it takes generally a bit of time to get to the core me. I was shocked that he actually got a pretty good read on me in a first meeting. That never happens. So this was a super interesting and new experience for me. I left the date feeling intrigued.
So we'll see, he wanted to setup a second date and asked for suggestions. I said yes and he has the ball, so It is up to him to schedule. We did text a bit over the rest of the weekend, more deep topics.
Anyway it is weird to meet people that are kinda similar and wildly different at same time. I think at a different point in my life, Mr. Easy would be a no-brainer. Now I am not so sure.
Mr. Easy sounds like fun, which is one thing you are looking for. Was me, he would be the 'winner' as his 'overall' sounds good, no issues, no 'complexes' (especially the part about him having no issue with your higher income potential). Sounds more like Mr. Easy-Going.
But, somehow, I don't think he will be the 'winner' with you.
Mr. Challenging turned me off immediately with the deep questions on the first date. I can understand wanting to be pushed out of one's comfort zone for sure, but I would want that with someone that I know and trust, not a stranger on a first date who does not know me. I don't like the word "intense." It's usually used as a substitute for someone who has an anger problem or seems ready to fly off the handle quickly. Coupled with the deep questions, I'd be put off. But you may not be.
Mr. Easy sounds like the "easy" winner between the two in my opinion but Mr. Challenging may set off more fireworks for you.
Mr. Challenging sounds a bit fake, like he's trying hard to tell you the things he thinks you want him to say....such as the whole schpeel about wanting an emotional connection before sex and asking you what sound like pre-planned questions to try and sound intellectual.
Which one are you physically more attracted to? Sometimes that can tip the scale one way or the other with two different people.
Mr. Challenging sounds a bit fake, like he's trying hard to tell you the things he thinks you want him to say....such as the whole schpeel about wanting an emotional connection before sex and asking you what sound like pre-planned questions to try and sound intellectual.
Which one are you physically more attracted to? Sometimes that can tip the scale one way or the other with two different people.
My guess is that Mr. Challenging is the 'better-looking' one... just a hunch.
Mr. Easy sounds like fun, which is one thing you are looking for. Was me, he would be the 'winner' as his 'overall' sounds good, no issues, no 'complexes' (especially the part about him having no issue with your higher income potential). Sounds more like Mr. Easy-Going.
But, somehow, I don't think he will be the 'winner' with you.
Mr. Easy is definitely easy breezy for sure. Other than finding time between kid duty.
Mr. Challenging most likely has a higher income than I do. Or it could be the same. And earning potential from this point on is mostly about choices we make in roles. I’m probably nearing my max, but he seems more ambitious about it than I am (same industry, same department, different types of roles).
Quote:
Originally Posted by cleasach
Mr. Challenging turned me off immediately with the deep questions on the first date. I can understand wanting to be pushed out of one's comfort zone for sure, but I would want that with someone that I know and trust, not a stranger on a first date who does not know me. I don't like the word "intense." It's usually used as a substitute for someone who has an anger problem or seems ready to fly off the handle quickly. Coupled with the deep questions, I'd be put off. But you may not be.
Mr. Easy sounds like the "easy" winner between the two in my opinion but Mr. Challenging may set off more fireworks for you.
I use the word intense as a code word for a bit serious or introspective. He seems to have spent a bunch of time and mental work on figuring out what he wants next. (Probably attends therapy regularly). But yeah I don’t know word I would use for intense in the angry sense. I am not super introspective so it is sort of a polar opposite for me. I am bubbly and cheerful. So most people seem intense compared to me.
Mr. Challenging was super direct. I know that can also be code word for rude, but that is not what I meant here. He wanted to put his cards on the table up front so people can select themselves out fast. But the questions while super deep felt a bit more academic than nosy if that makes sense. For me the hard conversations are always current feelings - I like to keep those close to the vest. I didn’t feel pressured in anyway to answer any of the questions. But getting his answers was very illustrative (they were not one sided).
Going out with Mr. Challenging was still a normal date with smiling, laughing, and flirting. But I didn’t leave knowing his favorite movie or sports team.
Probably what was interesting about having a more serious convo for me is that I am really good at conversations with strangers. And always get into shallow and frothy conversations with randoms on a regular basis. So it was completely new not to start there.
Both of these men are winning because they like to cook for their SOs. And have cooking together dates. Mr. Easy cooks all the time (he has sent me pictures) and makes his own ingredients, sauces, etc. Mr. Challenging went to culinary school. This is likely a reason to keep them both in the mix. Definitely high potential for fun future dates.
If I were dating--and this is just me, not telling you what you should do--I would go for Mr. Easy because at this point in my life, that's all I would want from dating: fun, companionship, laughs.
Also, I don't like intrusive questions like Mr. Challenging's. People like him take all the mystery and fun out of dating for me. He also sounds like he takes himself too seriously and is too blunt and direct, and like he was interviewing you for a job.
I often mention what I don't like about American dating culture, but one thing I do thoroughly enjoy when I encounter it is the light-heartedness and easy-going nature in a lot of men here. I think "happy-go-lucky" is the term. Mr. Easy sounds like one of them.
My guess is that Mr. Challenging is the 'better-looking' one... just a hunch.
Mr. Challenging is ever so slightly better looking, because has more personal style. These two are fairly similar in looks. Style does give you bonus points. But I saw a dressed up pic of Mr. Easy and he cleans up well. He doesn’t dress up on a daily basis but does when the situation calls for it. Mr, Challenging probably dresses up every day and puts thoughts in his outfits.
Mr. Easy is an immigrant from a different ethnic group than I am. And Mr. Challenging is the same nationality and ethnic group as me.
Mr, Challenging is definitely more outwardly confident than Mr. Easy.
Note: I called out income potential. I am pretty high income so a partner’s income isn’t high on my list. They need to make enough to support themselves and not be mad if I make more.
Quote:
Originally Posted by Don_Draper
Mr. Easy is also separated and not yet divorced. There's a child involved. That complicates things for sure.
Yup! Haven’t figured out his divorce plans or timelines. He told me his parents never divorced and have been separated and been in other relationships since he was like 7 years old. They are technically legally married, but dad has other kids and he has step-siblings and a step-mom. For all I know he might be like his parents and never divorce. I haven’t asked about that.
I think you need to stay open in these dating situations for as long as you need to. You sound genuinely intrigued by the second guy and comfy with the first but it seems that if you try to choose too quickly you'll end up not happy with either. So if you need to delay sex so you feel okay continuing to see both, then do so. You have a natural reason to delay with comfy guy since you don't even know his divorce timeline...you need to find a good reason for the other guy...ha.
I gotta say that once you decided to date again, you jumped in with both feet!
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