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Online Dating for the 2nd Time - A Journal


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Ha - and I'm going to need that energy this weekend... because when it rains, it pours.


- Out of boredom I switched my main OKC profile picture to one of me outside & smiling but wearing sunglasses. It's a decent pic, but I kinda look like a d*uche, unlike my previously more "friendly" photo. Despite that, as a result I got 15 new visitors (I usually only get 5 or less per day), 1 "Quickmatch" star, and two unsolicited messages, one of which was a rather cute 34-year-old. So I guess I now have a different perspective on what attracts women... and I'm questioning the whole "no sunglasses photo on your dating profile" advice!


- Unbelievably, 10 days after our last contact, REY messaged me today asking, "so whatever became of us meeting up?" Now, she knows full well what happened: she hemmed & hawed & remained unresponsive about specifics for a dinner date until 7:40pm, at which point I had to tell her I'd already eaten, but that I'd be up for another try if we planned things in advance. Then she closed her OKC account and I heard not a peep until now. I'm going to leave her message "unread" (it was short enough for the preview to display the full message) for a day or two, then call her and see about setting something up. Cautiously.


- At the end of her typically long daily message, tonight NIKO said she'd "love to meet this Saturday." FINALLY!


Which makes my schedule this week quite busy:


WED - Dinner w/ KIM

THU - Tentative dinner w/ VICKY but most likely will be canceled unless she contacts me first.

FRI - Dinner, dessert & movie w/ WYNN and I have a feeling she may stay the night.

SAT - Dinner w/ NIKO

SUN - Afternoon with Little Brother DAVY... and if I can snag REY (or even one of the others) for the evening, I'm gonna try!


Funny how now that I've eased up messaging new people this week, several previously noncommittal prospects are lining up at the same time. Inconvenient, but I'm not going to complain - this is what I was asking for, after all!

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You might need a couple of Red Bulls ! You must make good money to afford the dinners. Either that or


a) you have friends working in restaurants

b) you bring the dates to the same restaurant so they give you a deal

c) you use coupons.


b is actually a really good option, you can save money if you negotiate a deal with the restaurant, 20% off each bill provided you go there 5 times.

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I think OP has said he doesn't feel she is second best so I am not questioning his feelings. For me personally I would not be happy if a guy I dated and slept with bounced with the mindset that I am not as hot as his ex.


That's why we don't tell you where you land in our All-Time Rankings ™, or even that such rankings exist. Give us a little credit...

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- Another surprise. STEFANI messaged me after no contact for 7 days. The good news: she'd be up for meeting next week. The bad news: her uncle passed away and the funeral is this coming weekend, which explains her being "on call for a family issue" as she had mentioned last week. So I expressed my condolences, said I understood if she wasn't in a "going out" mood, and said I'd touch base this Sunday.


- NIKO messaged that this Saturday works for her, she's looking forward to meeting me, and that she'd like to come to my city instead of me coming to hers since hers is so boring! It's about a 30 minute drive. So far, so good.


- My dinner tonight with KIM went well. We talked a lot, she's great with eye contact, wore a dark & very sexy outfit of tight jeans, heels and low-buttoned shirt, and we had fun talking for a little under 2 hours. She even paid for half before I had a chance to refuse! However, she said she needed to look at some things a local artisan was making for her work tonight and also revealed that she typically wakes at 5am for her job. So I realized that we wouldn't have any post-dinner activity as I was hoping.


Nevertheless, I walked her to her car, went in for a kiss, and we made out for a minute. She's a great kisser, but I couldn't help but think it felt perfunctory, as if she owed it to me or that it wasn't a big deal to her. I'm definitely going to ask her out again, but I have a feeling that if things progress further that it will be more of a casual sex situation than a road to a relationship.


PS - I just realized that KIM is actually JOY from page 4. I changed the name accidentally at some point... but obviously this tidbit is only for the nerdiest of those paying attention to this thread!


Looking forward to my "evening off" tomorrow!

Edited by NorthDallas40
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You may have answered this already, but how do you normally message the girls you are interested in? I ask because that could be a reason for your low rate of responses, as a women I get a lot of messages and that first message plus a red flag in the profile is a reason to not respond. Like, if your first message is "what's up?" I normally don't respond unless you are really attractive or your profile stands out. Also, no picture=no response.

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You may have answered this already, but how do you normally message the girls you are interested in? I ask because that could be a reason for your low rate of responses


Haha it's funny you ask this question *now* when I had a date last night, have one tomorrow, another this Saturday, and possibly two more if the girls are serious about meeting. And since I moved a secondary photo to the primary position the other day, I've gotten several unsolicited messages and many more visitors. I'm actually needing to take a break from meeting any new people at the moment; my schedule is filled!


But to answer your question, I have 10 photos (6 of them recent, the others 1-3 years old) and two of my female friends on OKC said that my profile writeups were not only good, but they felt like they needed to improve theirs after reading mine... and theirs were great already IMO!


Anyway, here's a sample note I sent last week with no response:


Hey ______ -


You've got good taste in movies & TV shows - have you seen the UK show MISFITS? Since you like SKINS, you might dig it!


That's also cool that you like to hike - do you ever visit the ________ Trail in ____?


Anyway, you seem like an intriguing person so it would be great to hear from you,

- ND40


I always address the woman's interests, never just say "hey," and I sometimes write a slightly longer message if I feel inclined.

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Along with laundry & chores I did a round of calling / texting / messaging tonight:


- Left a voicemail with REY about meeting if she's up for it.


- Left a voicemail with NIKO and emailed her plans for Saturday. She just texted that she saw my missed call but didn't get my voicemail.


- Earlier in the day I texted WYNN to see if she wanted to hike or go to the beach on Saturday but she had already made brunch plans. We're still on for Friday night though.


- Called DAVY after work about our Big Brother meetup on Sunday, and just emailed some activity ideas to him & his mom.


- Ignored several unsolicited OKC messages. Jeez, that new profile photo is really doing the trick, if not exactly attracting the kind of woman I'm looking for.


- VICKY never got back to me, so she's out.



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- My date with WYNN was another good one last night: dinner, dessert, strolling, movie, lots of laughing, and a healthy makeout session in her car. She declined my invite to stay over, but she lives 30 minutes away, had plans for this morning, and given my past behavior I don't blame her for being more cautious as well.


- I called KIM today to leave a voicemail about a 3rd date, but she was taking a bath when I called so she actually picked up! Our conversation was brief but she said she's up to meet after next weekend. The delay is because she's busy with 3 birthdays this weekend, preparing for a trade show this week, and going out of town for that show next weekend. At that point she said her schedule should be easier, and she apologized for being so difficult to pin down. I said I'd touch base next weekend which she said sounded good to her.


- NIKO emailed & texted yesterday, quite flirtatious and excited about our dinner & miniature golf(!) date tonight. She's definitely built up some positive expectations in my mind, so I hope she's as charming in real life as in her messages.


- Talked to DAVY's mom today and we finalized my aviation museum & biking outing with him tomorrow.


- No word from REY yet, but really, who cares. She apparently just wants attention, and I didn't find her voice attractive on her outgoing message anyway; she seems like kind of a bummer.

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Why is Kim on a dating website I wonder, she has no time for a bf.


Well, I noted earlier that in the same message in which she confirmed our first brunch date, she admitted she may have joined OKC too early considering her current work schedule. And soon after our first date, she took down her OKC profile entirely and it's still not up... which I suppose bodes well for my chances! But to her credit, she's never flaked on me, and all of her excuses have checked out. Even tonight I looked at her online photo sharing account and sure enough there were b-day party pix from both yesterday and today as she claimed.


As for the other irons in the fire...


- My date with NIKO last night was good, even though when we arrived at the mini-golf place it was booked solid! Luckily that gave us an hour to stroll in a nice shopping district and talk before dinner. She was charming, cute, intelligent, stylish, friendly, had a good sense of humor, and shared common ideals with me. There was a bit of a language barrier (English is her 2nd language but she has a good grasp of it), but we had a very nice time. At the end of the night, I went for a kiss but got a cheek, which was fine because she admitted via text today that she was actually a bit nervous though she had a lot of fun.


My Big Brother outing was in her area today, though, so I invited her to dinner & the new STAR TREK movie tonight since she likes SF films. She accepted very quickly and again we had a good time. But in the end I've decided I'm not 100% attracted physically and the language issue makes fine shades of communication difficult. Plus she lives 30 minutes away AND tends to go to bed very early, which would make weeknight dating impossible. Unfortunately, she left her sunglasses in my car so I'm going to have to send them to her rather than give them back on a 3rd date!


- I messaged STEFANI that Wednesday works for me if she's up for going out so soon after her uncle's funeral.


- WYNN and I texted a bit yesterday and she's up for another date.


- I messaged 3 new people on OKC today and got back 1 response. This time from a new-age yoga chick who claimed she stopped being vegetarian "because i love to meet many different type of people which makes easier to hang out with people without being vegetarian" which is the biggest load of bs I've ever heard on the topic. Soooo tempted to tell her so, too... but I'll just let it lie.


- And my first outing with Little Brother DAVY went really well today - we both had a great time and I got to visit some places I'd never gone otherwise. Total win-win!

Edited by NorthDallas40
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- I messaged NIKO that I didn't think we were a match and she agreed, so that was painless. Just need to send her sunglasses back!


- STEFANI got back to me and said she still wants to meet but she caught a cold, so next week would be better for her.


- Unsurprisingly, REN never returned my phonecall from Thursday. Typical textbook flake.


- Yesterday I got a first reply from MARA whom I first messaged over six weeks ago(!). Her picture wasn't clear, though, and now that she's added a couple more, I'm not sure if she's attractive or just not photogenic. Need to think about this one.


- And in going over old messages, I realized I got a reply from CELINE when I was out of town almost a month ago that I never replied to, other than to say I would message later. Like MARA, I can't tell how attractive she is (1 pic is beautiful, 2 are so-so) but I sent her an apology and invite to meet or chat on the phone this week.


- I usually play soccer on Tuesdays (tonight), but this time I decided to catch a couple of movies at my usual repertory film place instead. I invited IRINA's gay friend HANK to go, but he was busy. Then last night KAY invited me to a comedy club at the same time as the movies so I declined. But today IRINA told me she had some free tickets to a concert tonight that she couldn't attend. I knew KIM would dig the bands, so I asked her if she wanted to go the concert... but she was busy. So the movies it is, and even an open invite on FB yielded no takers for my extra ticket. Darn.. after this flurry of messages to various prospects, I'm going it alone tonight!


- Luckily WYNN and I have firmed up plans for a picnic + museum + movie date this Sunday, which I'm pretty sure will end up with dinner and her staying overnight.


Which I'd be more happy about if I hadn't had TWO dreams about KATE this week:


- In one, I was cutting my hair (and injuring myself in the process) while we talked in the bathroom, and though she was smiling, whatever she was saying to me was so mean that it prompted me to ask, "You enjoy hurting people, don't you?" To which she responded, "Don't you?"


- Then last night's dream had her helping me on some mad errand where I had to run after her. Though we were still together, I knew she was going to break up with me as soon as we were done. I just had to keep a brave face despite feeling devastated.



Edited by NorthDallas40
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I just wanted to address something that Blue Spiral said in reference to this dating journal in the thread at



Actually, I was talking about the fact that you've invested a ton of time and money into women, and not gotten much in return. You let yourself be used for entertainment and meals, and you've somehow rationalized that it's a good, fun thing, and that anyone who's against being used is somehow immature.


If dating women (and actually PAYING for the date) in order to begin a relationship is "immature," so be it. At least I'm in good company... with almost every other single guy out there!


And regarding your claim that I'm "not getting much in return" - sure, I don't have a girlfriend yet. Call me a failure if that's the only litmus test we're using here. But as I said in this thread:



• I've made a couple of good / interesting / fun friends who I still stay in touch with on a platonic basis


• I've discovered several new restaurants & activity spots I didn't know about until I researched them for dates


• I've been on the town with several very attractive women for a night (or two... or more)


• I've met some really interesting women (and yes, a few boring ones!) from around the USA and the world


Sure it's frustrating that I'm still not in a relationship yet.


But if I chalked up all these experiences as "failures," that would say more about ME than the dating process.


It's a game in a way... so win or lose, just enjoy playing it!


Besides, I'm hardly being "used." I take the initiative to ask a girl out, and I pay for the first date. It's the polite thing to do and makes sure that I'm putting my best foot forward from the outset.


And FWIW - my last dates with KIM, KAY, NIKO and WYNN all had them paying for at least half of our outing. I'm hardly at doormat status yet.

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I sent out a few new OKC messages since my last roundup post and got a couple of responses.


- GLORY sent me a lengthy reply about Ayn Rand(!) within minutes of my message last night, so I engaged the discussion and we've continued it today. I have reservations since she doesn't have any full body pics, but her face is super cute judging by her 4 photos. Luckily she seems intelligent & interesting (if a bit cynical) regardless of body type.


- In contrast, very attractive DAISY sent me a couple of short and not very eloquent replies, but I got her phone number so I'm going to call tonight. She seems like an airhead, but hey you never know.


- I also replied to ROSE, who had sent me an unsolicited first message a few days ago. She seems pretty & intelligent, so I asked if she was free this weekend.


- I even replied to "New Age Yoga Chick" AURORA from a few posts ago, gently ribbing her for her reasons for not being vegetarian anymore and asking her out for this weekend as well. I don't expect a reply, just rolling the dice.


So for phone followups I'm going to call DAISY tonight, and call STEFANI and KIM on Monday.


And in real life dating, IRINA and I are going to a show tonight (platonically) and WYNN & I are on for Sunday (definitely not platonically).

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Oddly enough, new age yoga girl AURORA got back to me... but with a vague, non-committal reply that leaves the door open for her to flake:


Healthy dinner and brunch sounds good. Saturday brunch maybe possible but not sure. I will let you know Saturday morning. I cannot make my schedule any farther then next day now.


I'm not about to wait til tomorrow morning for a confirmation on brunch that same day, so I tried to pin her down a bit:


Brunch on Saturday sounds perfect. Whereabouts are you located? I'm in ______. Just confirm by 7pm tonight so I can find some spots convenient to both of us. And if you can't confirm by tonight (tomorrow morning is a bit too late notice for me; I like to plan ahead!), then we can try for dinner next week.


And in other yoga news, a very cute new tenant MICHELLE (who's also a yoga instructor as I found out last night) moved into my apartment complex two doors down a few weeks ago. She cheerily introduced herself and already knew my name because she claims our property manager gave it to her. FWIW, our property manager has never told me any other tenant's name before.


I didn't see her again until last night when I came home around 10:45pm. She was in a lower level apartment hanging out with the guy she previously sublet from, and their door is open.


I passed by his door to get my mail and by the time I passed by again, she was leaving his place at the exact moment to follow me up the stairs to her apartment.


I turn around to say hi, she smiles and says "you're not home very often!", remembered my name (as I did hers) and we chat for a minute. The whole time we talk she's facing me, smiling, keeping constant eye contact and when I say good night, she doesn't seem quite ready to stop the conversation.


Was she flirting? Not sure, but I'm going to make the effort to talk to her further if I see her again. Does the old "do you have any sugar I could borrow?" trick still work?

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Well what I'd hoped would be a promising weekend has already turned out to be less than great and Friday's not even over.


- DAISY texted me tonight, I called back and we had a nice 45-minute chat. She's a nurse and seems like a sweet person; not at all the airhead I thought she'd be. But she revealed that not only is she 3 months separated, but she also has a 16-year-old son, which she did not say in her profile. She's going out of town this weekend and I said I'd call her next week, but I'm not really looking for a relationship with a single mom whose last relationship ended so recently. I'm up for meeting at least once, but I'm hesitant.


- AURORA messaged back this evening, not surprisingly to tell me she's unavailable for brunch tomorrow. I messaged back "No problem - if you'd like to meet in the future, just let me know" and I'm going to leave it at that.


- GLORY sent a very brief reply to my last message; so short that I think she's bailing on conversing further. I'm going to send her another message this weekend, but I don't expect things to progress from there.


- I didn't see my neighbor MICHELLE today, but I did see a guy smoking outside of our complex who then unlocked the door to her apartment. I'm hoping he's just a roommate since I've been able to deduce she has lots of gay friends, plus I wouldn't think a yoga teacher would date a smoker... but obviously he *could* be a boyfriend. Either way, I'm not going to worry about it until I see her again, and who knows when that will be.


- But the most disappointing news was from WYNN. We talked on the phone tonight and despite our having plans for an all-day outing this Sunday (and even discussing details about it today over email), she said that things feel different than in January and that she'd rather not continue seeing each other. She said it wasn't because of another guy, but simply that her heart wasn't in it this time around. Since I basically did the same thing to her 4 months ago, I was understanding. We agreed that we have a lot in common, though, so maybe sometime in the future we could be friends.


I'm disappointed, but I don't regret calling things off back then, nor keeping my options open this time around. I was always honest with her, and did what I felt was best for me in both instances. I knew that losing her was the risk I was taking, and I accepted that. Now that it's happened, I'm already feeling sadness but it should pass soon enough. I hope.


So first KATE dumps me, now WYNN does the same thing, leaving me with not many prospects.


DAISY is a possibility but she has a kid which I'm not so keen about. STEFANI is on my "to call" list, but after a month of trying to schedule something, we haven't even talked on the phone yet. And though KIM claims her schedule should be more flexible after this weekend, I'm not counting on things going much further with her since she's not exactly been enthusiastic so far.


In short, nobody else is realistically in the running at this point... so after all this effort, I'm basically at square one again.


( ...are those echoing "I told you so"'s emanating from the ether courtesy of Ms. Darcy and Blue Spiral? )

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Kinda difficult afternoon.


I drove to NIKO's town to return her sunglasses and stopped at a record store on the way. And what vinyl 45 did I find but one called "WYNN IS GONE" (using her real name of course)! I took a photo and texted it to WYNN saying "what irony!" knowing she'd see the humor.


When I met up with NIKO at her work, she seemed glad to see me and expectant for me to talk more than I did. She actually appeared a bit sad that I didn't stay long, and I wondered if she thought that my seeing her in person meant that I had changed my mind about not seeing her again.


But by the time I got back to my car, WYNN had texted back, laughing about the 45 picture and telling me something funny she saw today. Dammit, it's just so hard to believe she wanted to cut things off this time after only 3 dates this time around, when we seemed to be getting along just as well as ever. ***!


Before I drove home, I passed by a cultural center where KATE's family had a booth at one of our last outings, and stopped in a specialty supermarket that KATE liked, and that I'd only visited when with her. I even saw a woman at the market who looked JUST like a 25-years-older version of KATE, even down to the hair, blouse, scarf, skirt and shoes. My stomach was churning the whole time.


As for my other prospects, I messaged GLORY about meeting this week and she read it, but no reply.


And I checked KIM's online photosharing account and not only did she go out to a bar and concert on two nights this week, but she went hiking with a male friend last night when she had that out-of-town trade show today! I realize she has a life, but the fact that she told me that this week wasn't good to meet up, yet she did all sorts of fun stuff anyway... well it kinda hurts. Or at least lets me know that her interest level in me is pretty low. Ugh.


So yeah, dealing with all the mixed emotions today has been rough.

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Just a question ND40 (and not meant to put you on the spot or antagonize): What makes a man stop wanting to keep his options open? I'm asking in all sincerity because, well, I'm just wondering what would make you NOT want to risk losing someone that you think has potential. What could Wynn have done differently back in January that would have made you NOT want to take the chance you might lose her for good? I know you mentioned some superficial things -- like her height, if I remember correctly (forgive me if I'm recalling this wrong), but...anything else?


I guess I'm just trying to understand what makes a man decide, "This one's worth pursuing. I don't NEED to see anyone else to know that."


I'm single, 42, and wanting to meet someone, but I have to admit that, while I am totally rooting for you to find the right woman for you, this thread makes me not want to meet people online at all because I fear that I won't have that whatever-it-is that makes a guy feel like he doesn't need to "keep his options open." I'm educated, well-groomed, attractive (from what I heaf, anyway!), have a great career, am a homeowner, exercise 5 times a week, have lots of interests, a great circle of close friends, am, told I light up a room, am well-liked, etc. -- but..I don't know...I feel like there's something SO specific ya'll are looking for, and I have no idea what that is!

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All I can say is that when I got to know KATE (and before I got to know her better, my ex MARIA a few years before), I just knew I wanted to be with her for life as long as she felt the same way about me. It was a gut feeling.


As for Wynn....


First off, I met her when it was too close to my breakup with Kate for me to really give her a fair shot and not keep making comparisons. I realize that now.


But besides that, she seemed to have some "walls" put up from the beginning that Kate never had. I hadn't even gone out with Wynn a few times before there were some hiccups and slight personality differences that I think made both of us pause a bit in our feelings for one another. Never the problem with Kate.


And as for my personal preferences with women, I had a problem with Wynn not being a particularly flirtatious person, and seeming a little lacking in confidence. Kate was great at flirting even if she didn't say a word, there was always a (tasteful) undercurrent of sex even when we were just walking around, and she carried herself like a confident, poised woman.


Wynn - though quite attractive - often seemed like a nervous child, or conversely, a prudish older woman - probably because she was a schoolteacher and dealt with kids a lot. Though she was great in bed, she never gave the signs. I was genuinely shocked when I kissed her the first time and she reacted positively; I had no idea how she felt about being physical because she simply didn't give any hints beforehand.


Now in terms of other things, they were both intelligent, kind, funny and caring - pretty much a dead heat there. But Kate was a better cook and brought more cultural / family / friend aspects to the table. Plus Kate was vegan and wanted kids, while Wynn did not.


And to be honest, Kate made me feel like a man in every regard. Wynn made me feel like I had a really good buddy.


And that's a big difference when you're looking at having a relationship with someone for life... ESPECIALLY when you're making that comparison within two months of each other.

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I fear that I won't have that whatever-it-is that makes a guy feel like he doesn't need to "keep his options open." ...I feel like there's something SO specific ya'll are looking for, and I have no idea what that is!


Hey, it's not just women who feel that way!


I have a good job, car, apartment, am in great shape, have a good circle of friends, many hobbies & interests, am a good cook, reasonably good-looking (well a 6 anyway ha!), have most of my hair, disease-free, don't smoke, light drinker, great with kids, dress well, can adapt well to almost any social situation, no anger issues, etc.


But I can't help but feel that women look at two things: a) my looks and b) my income level, and won't go further if those don't measure up.


I mean, both KATE and MARIA said I was an amazing boyfriend when they dumped me... so why couldn't they make it work!??


So believe me, both men and women feel the pressure.

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I'm sorry things didn't work out with Wynn. I've been following this thread and was rooting for that match.


I think it's pretty obvious that Kim is not into you. I hate to see you keep pursuing her so earnestly when she continues to give you the brushoff. I'd let it go and press forward.

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