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Online Dating for the 2nd Time - A Journal


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A few years back, I posted a journal of my online dating experiences:



A couple of relationships later, I was finally dumped in November and tried to get her back in March:



That didn't work, so I went through some self-examination:



Now I'm back in the singles game... so here's Round 2 of an online dating journal from a 42-yo guy in a big American city.


I have accounts on POF & Match.com, but the former seems a bit sketchy and the latter has never yielded any results for me.


So for now I'll be focusing on OKCupid, which has been pretty effective for me in the past and is how I met my last two girlfriends.


Back in December 2012, I sent out about 50 messages on OKC which yielded 5 dates:


JINA (29) - We went out twice, held hands on 2nd date, got along well but no real sparks. I halfheartedly asked for a 3rd date a week after our 2nd one, but she didn't accept and I didn't really care one way or the other.


TISA ( 38 ) - Very professional type-A personality, talked about herself the entire dinner, messaged me later that she wasn't interested anyway, so that was it.


ELLEN (42) - Had a nice 2-hour lunch but she wanted to be just friends; we're pals on FB now.


IRINA (42) - We had a fun date, but I wasn't interested in pursuing further. A few months later she contacted me on FB because we had a mutual friend, and now we hang out every so often as each others' wingmen haha! Great friend now.


WYNN (37) - We got along well from the first email, lots in common, communicated a lot, sex was great, we ended up dating every weekend for 5 weeks. But then I had strong reservations (some identifiable, others not) about getting too serious, plus I hadn't quite resolved feelings about my ex, so I called things off. I still think about her every day, though, and would seriously consider contacting her again if other options don't pan out. But admittedly she may not want to give me another chance, may be dating someone (after being on OKC this entire time, she took her profile down today) and I really need to play the field a bit right now before I'd feel comfortable going back with hat in hand.


Then IRL, a very pretty longtime friend & former bandmate SASHA (31) drunkenly hinted very that she was interested in me when we saw each other at a club a few weeks ago. We've been friends awhile but she has boyfriend, so I took that with a grain of salt and just texted her a week later about meeting for a drink next time she's in town. She said she would, but I'm not holding my breath for a date, nor will I do anything past a hug until she breaks up with him. I just wanted to let her know the door was open.


Since my last round of OKC dating in December, I have a new photo with short hair and I've edited down my profile to keep it briefer, and also to emphasize my more responsible traits that might appeal to women more serious about a LTR.


I've sent out 90 messages, mostly to very attractive women so I've expected a lot of non-replies. I sent 3 of them just to have an activity partner for moviegoing (1 didn't reply; 1 agreed, we talked on the phone for an hour, but she ultimately flaked; 1 lives in another city but will be moving here soon, we're now FB friends). 11 messages were never opened. I got lukewarm replies from 2 women that didn't go anywhere.


Then after a long drought of no replies at all, last week I received 4 (!) replies that showed clear interest, and here's the results after a bit of back & forth:


JEANETTE (41) - Financial Analyst. We talked on the phone for 45 minutes this past Friday and have a date tomorrow (Tuesday)


RAQUEL ( 38 ) - Graphic Designer. I plan on calling her tonight, but we have a concrete date for Wednesday regardless.


NICOLA (33) - Not sure of her job, but she's nerdy in a good way. After some lengthy replies at first, her messages got briefer and less frequent, and though we have a date set for Thursday, the specifics aren't nailed down yet. I think there's a decent chance she'll flake.


KATHY (41) - Psychologist. I've only gotten one reply so far, but it was enthusiastic, so I asked to chat on the phone this week. Still waiting on a reply.


In between all these, I get around 3-7 messages a week from women I have absolutely no interest in.


So 90 messages this go-around have yielded 3 dates for a success rate of 3%, down from from a 10% success rate in November. And to be honest, I'm not super excited about any of these four women yet, but I'll reserve judgment until I meet them IRL.


At least I'm keeping busy this week.

Edited by NorthDallas40
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Of course! I'm the man, I'm asking them out, it's the right thing to do.


Agreed. I was just wondering, as that can be costly (I'm 40 and am thinking of delving into this for the first time, though admittedly with not much disposable income at the ready)

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Agreed. I was just wondering, as that can be costly (I'm 40 and am thinking of delving into this for the first time, though admittedly with not much disposable income at the ready)


You bring up a really good point because yes, it can be QUITE costly, especially if you don't take a good look at the menu prices beforehand. I neglected to do that once and ended up with $90 bill on a very mediocre date!


But you can manage the costs by deciding on restaurant choices yourself beforehand. Ambience and good food don't have to be expensive, and with a little research you can find some options that won't break the bank. And of course there's always inexpensive activity options if you think outside the box (walking in the park/beach/hiking, free art openings, free club nights, etc.).


Besides, women LOVE IT when the man makes the plans first. Nothing more unattractive than a guy who says "I dunno, what do *you* wanna do?" (cricket chirps)


I try and find out what kind of activities/food the girl likes first, then find inexpensive but appropriate & impressive options, give her 3, and let her decide. You end up looking like a man who can take charge... without being over charged! (I know, groan...haha!)


And for those guys out there who don't think it's worth the effort, here's the last message from Raquel after we finalized our plans:


"oh.. and thanks for doing the leg work on this! I'm usually the one that ends up doing the research so this is so appreciated!"


See? I'm already in the lead and we haven't even met yet.


So be a good date, guys!

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Well when it rains, it pours.


Kathy still hasn't replied, but I talked to Raquel on the phone last night to confirm our date tomorrow. She's a bit of a talker, but that's probably good for a first meeting.


Then this morning I messaged about 4 girls on OKC and one of them, Elle (34, apparel designer), replied, and accepted a lunch invitation for this Friday - one of the quickest dates I've ever set up.


Her profile had some red flags that indicated she might be fragile/damaged/cuckoo, but we had some very specific things in common so I think that helped seal the deal. We even have some mutual friends in town, as well as ones from a state halfway accross the country, and she said that put her at ease about meeting me. Interestingly, I noticed after our convo that she edited her profile to be more positive and less bitter. Hopefully that's a good sign, but I'm treading *very* carefully with this one... plus she's very tall & attractive, which is sometimes a red flag in itself.


Then after almost 2 days of non-replies, Nicola confirmed for Thursday and even gave the thumbs-up for an after-dinner activity I suggested.


So I've got 4 dates for the next 4 days... yikes.

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Date #1 with Jeanette went well last night, especially since her very first words to me were a surprised-sounding "Wow, you look GOOD!" It was quite an ego-boost, but I chalk it up more to her possibly having some busted-looking past OKC dates than me being particularly handsome.


Anyway, she looked great too, better than her photos and I found her very attractive. Unfortunately she's not vegetarian, wasn't a particularly good conversationalist, and I don't think we have much in common. I'm not sure something long-term would really work for us, even if both of us tried.


But she's intelligent, pretty, well-dressed, carries herself well, polite, not afraid to speak her mind, knows how to flirt subtlely, has a good sense of humor, and we didn't have any awkward moments during dinner or the comedy club. At the end of the night, she gave all the right signals so I kissed her a few times and though we didn't make out, I could sense it was just because she wanted to take it slow.


She clearly enjoyed our evening (including the kissing), so despite my reservations, I'm going to ask her out for a 2nd date. I'm pretty sure she'll accept, but I'm not really sure if it will lead anywhere more serious. But I guess that's what this whole process is all about.


And for those keeping score, dinner was $36 including tip (we fortuitously hit happy hour at a dim sum place so that helped), and the comedy club was $30 including 4 drinks (again, we lucked out with it being ladies' night so she was free and my admission was only $5, plus she doesn't drink alcohol so her tea was very inexpensive!). Total damage was $66 and was well worth it IMO.


Date #1 with Raquel is tonight.

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My date with Raquel last night was ok. We met for beers & dinner, she was petite & cute, we talked effortlessly for 3 hours, and it was generally a pleasant time. But from the moment we met, I could tell from her body language that she wasn't looking at the date as anything serious. She didn't make much eye contact and fidgeted a lot, though I got the feeling she's fidgety anyway. She was a total 180 from Jeanette the night before, who was calm, poised, and maintained very warm & inviting eye contact the whole evening. With Raquel it felt like I was having a platonic dinner with a friendly but harried coworker.


But to be fair, I wasn't immediately attracted to Raquel either (she was a bit talky & high strung for me) so after a couple of hours I didn't mind letting our conversation drift onto dating & past relationships, topics that should almost always be off the table for a first date with potential, but is one of my favorite things to discuss with female friends. Soon it became clear that she was still a bit hung up on a past relationship (and dating in general) so I was happy for us to use the time as a mutual relationship therapy session.


The final bill including tip was $56, but the meal and microbrew beers were great so I didn't mind the expense. I'm going to PM her today that I had a nice time but I don't really feel we were a match.


As for Jeanette, I messaged her yesterday at lunchtime about meeting again and though she read the PM, she has yet to reply.


Elle hasn't confirmed the time for our lunch tomorrow, but since the ball has been in her court for two days and she seems flaky anyway, I'm not going to bother prompting her for a confirmation. If I haven't heard from her by midnight I'll consider the date cancelled.


And I also noticed that Wynn's profile is back up on OKC... so I'm still seriously considering contacting her in the future.


Anyway, I have date #1 with Nicola tonight: dinner, comedy club (not Twister! haha), and she even offered to bring a bottle of wine since both places are BYOB, which I appreciated. I have a feeling we'll get along great (she's smart, knowledgeble, vegetarian and loves to cook) but I have suspicion she'll a bit on the tomboyish side. I really hope that is not the case because I prefer women who are more feminine (like Jeanette). Fingers crossed for a smidgen of makeup, jewelry, and/or heels instead of a ponytail and Chuck Taylors!

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I had some free time today so I pared down my OKC favorites list. I weeded out the crazies, the ones I'm not really attracted to, ones who are looking in a younger age range, etc.


And in the process I sent out a whopping 22 messages to new people. But again, I'm expecting only 0-3 responses at the most.


I also ended up sending Elle a quick note about tomorrow, Raquel felt the same way about not pursuing anything, and still no reply from Jeanette about a 2nd date. Date w/ Nicola in 1.5 hours.

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Last night's date with NICOLA was 4.5 hours and went very well...except for getting a ticket for a burnt-out headlight! Dinner was delicious, the wine she brought was superb, the comedy club was hilarious, and our conversation was genuinely interesting & fun all night. Total was a bargain $66 for a fairly upscale meal, club & parking.


There was just one problem. From the second I saw her, I knew I wasn't attracted in the slightest.


Though she was tall & slim and not tomboyish, she wasn't particularly pretty (she only had 1 photo on her profile, always a red flag), her voice & laugh were unappealing, and even her mannerisms totally turned me off. Though I'm a reformed nerd myself, she was way too nerdy even for me, and not in an endearing way. I need at least a little bit of feminine appeal with the women I date, and she had very little, though she was a very nice, enthusiastic & interesting person.


So though it wasn't particularly late after the show was over, I just dropped her off at her car and wished her a safe trip home. She texted me 30 minutes later saying "thanks for a wonderful evening" so I felt I did my duty in showing her a good time. But this morning I PM'd her politely that I didn't want to pursue anything further.




ELLE eventually replied to my prompting about today's tentative lunch date, but with predictably flaky results. At 10:40pm last night she said she was still on, but by 1:20am she cancelled, claiming "I can't tomorrow - i ended up getting booked with work. But lets try another time."


I found it hilarious that I was supposed to buy the "I got booked at work" excuse when it could have only happened between the hours of 10:40pm and 1:20am. But that's par for the course with someone who's not really interested.


I just PM'd back "Sure - just holler back when you're free" and I don't plan on contacting her further unless she initiates.




As for my 22 new messages yesterday, almost half of them still haven't been read, but I got two nice replies by the end of the day.


EDNA (42) - We have very similar music/movie tastes and we agreed we'd probably get along great. But she said she wasn't vegan nor is she likely to have kids, plus she's going out of town for work for a few months. I just told her to drop me a line when she gets back and if we're still both single we can take it from there.


AMY (34) - She gave a fairly lengthy, intelligent & friendly reply to my very brief message, and I liked what she said re: movies, food, and Big Brother program. So I replied with an equally lengthy response and said I'd love to chat on the phone and/or take her to dinner next week if she's up for it.




And finally JEANETTE replied to my invitation for a second date with a yes. She wasn't sure of her schedule for the weekend, so I PM'd her some date options (dinner, lunch, hiking, museum, amusement park, movie, dance clubs) for all three days. I basically made it so she has no excuse not to take me up on at least ONE of my suggestions... though I don't think she needs too much convincing. I'm just hoping our conversation goes better next time around!

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Hahaha! It IS work! Very time-consuming too. Especially when I'm writing long-winded wrapups here on ENA


But for me it's worth it. I almost always have a good time on the dates, I'm learning more about the city as I look for activity options, and it's great practice for when I finally meet the girl I really want to be serious with.


Besides, I'm going to be 43 next month... the quicker I can separate the wheat from the chaff, the better!!

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See guys ... women do respond to online dating messages! Go NorthDallas.


They do... but it's really a numbers game. The more women you message, the better chance you have of getting a response. That's just the fact of the matter.


And it's essential to tailor your message to a woman's profile, make a gently humorous comment if it's appropriate, and ask a couple of questions so they actually have something to respond to. I don't ever write "hi!" or "Hey sexy", nor any kind of cliche pickup lines. Each woman I message gets a fairly "tailor-made" note, but I don't ever EXPECT a reply. I write, move on to the next one, and hope for the best.


And on a slightly sexist, but important, note: I want to clarify that the most attractive women (the 8s, 9s, and 10s) are NOT messaging me back. I'm mostly getting responses from 6s & 7s.


As I've said, I'm ok looking and in shape. But I'm not young and by no means a Brad Pitt, so the Angelina Jolies of the dating world aren't going to be banging down my door. So I understand & accept that.


But on the bright side, since I'm not particularly photogenic I think most girls who *do* go on a date with me end up being impressed IRL because they've set their expectations low based on my pictures haha!


I think a lot of guys would save a lot of frustration & anger towards women on dating sites if they a) took a good hard look at themselves and be honest about what they have to offer a woman, b) realize that the more attractive a woman is, the more messages she's going to get from guys better looking than the average joe, and c) adjusted their own expectations accordingly.

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Date #2 with JEANETTE went really well... with a bit of a hiccup (IMO) at the end.


I picked her up outside her place, we went to dinner, strolled along a local tourist amusement park for awhile and had tea afterward. The date lasted almost 6 hours, and luckily the conversation went much better, and any awkward moments were short. I did most of the talking, but I realized she just prefers to listen rather than talk about herself. Throughout the night her eye contact & smiling was just as inviting and poised as before. While we walked, I held her hand, put my arm around her, and she took my arm and it felt very comfortable. I even massaged her feet discreetly underneath the table while we had tea since she was a little bit in pain after doing all that walking in heels. There's no question we both enjoyed a very romantic evening, and it felt very good being with her.


But while we were sitting in my car when I dropped her back home, it got a bit confusing.


She told me she had a nice time & thanked me for everything.

So I went for a kiss, expecting a bit of a makeout session since we'd already kissed before.

But she adamantly didn't kiss back, gave me her cheek, and just kept smiling.

"No kiss tonight?" I asked, keeping a dumb smile on my face out of confusion.

She just smiled, looked down, paused, looked directly at me and asked, "Are you tired? You look tired."

"No I'm not tired."

"Maybe it's just the light."


Then still smiling and keeping eye contact, she took my hand and said "So will I hear from you this weekend?"

"Do you want me to?"


"Then sure. The other plans I gave you for the weekend are still on the table. The movie on Sunday looks good."

She smiled and said "Ok - I'll look it up."


We said our goodbyes, and I drove off wondering what the heck just happened! I don't mind taking things slow, but I prefer steady ESCALATION, not some "1 step forward, 2 steps back" business.


I'm going to message her today about doing something tomorrow, but quite frankly if we don't at least KISS by the end of the night, I'm not sure I want to continue stretching things out.


Women of ENA: if you can offer your views on her behavior and/or my expectations, I'm all ears!




I also got a reply from EDNA saying that she doesn't leave town for a month, so we could meet before then. I'm going to PM her tomorrow about setting something up.


I haven't had any other OKC replies yet, but almost nobody replies on a Friday or Saturday; Sunday evening is usually when most people become most active on the site.

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I guess she just really want's to take it slow, personally if I had already kissed the guy on the first date, I'd definitely kiss him on every date after that. I guess see what happens today, if there's no kiss again and you don't want to move that slow, don't see her again. I do think she likes you though.

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Yesterday I texted Jeanette to see if she wanted to go out tonight; she said she may have plans (which she told me about on Friday before our date), but said she'd contact me this afternoon.


And I just messaged 20 more women on OKC. Ugh, it's like a 2nd job!


That's kind of bad form .... to text for a date (bad) and to text for a date the only one or two days after you ask (bad). You seem like a guy talking to a bunch of women at the same time.

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That's kind of bad form .... to text for a date (bad)


For a first date, I agree. The first time I asked her out, it was at the end of a 45 minute phone call.


But after we'd just spent SIX STRAIGHT HOURS talking to each other in person the night before, I don't think texting for a 3rd date is bad form at all, and past relationships have borne this out. Some people actually prefer texting once you've gotten to know each other in person; no problem with that.


and to text for a date the only one or two days after you ask (bad).


I'm not exactly sure what you're saying here.


But to clarify, on Thursday I gave her options for all three days of the weekend because she said she might meet with a girlfriend on Sat or Sun. We went out Friday and that night she asked if I would contact her over the weekend. So the next evening I texted about doing something on Sunday night. She replied that once she heard from her friend, she'd text me Sunday afternoon.


This is bad how?


You seem like a guy talking to a bunch of women at the same time.


So if you went on a really nice 6-hour 2nd date with a guy and mentioned you'd like him to contact you over the weekend, and he texted you the next afternoon asking for a date the next night, you'd assume that a) he has bad dating form, and b) he's talking to multiple women?


That seems like a lot of assumptions to make from a text vs. a call. Most guys dating multiple women would allow a week to pass before a 2nd date, not schedule three of them in the space of five days! If anything, I'm probably coming accross as too eager to date just her alone.

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