Online Dating for the 2nd Time - A Journal

[NorthDallas40]

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.

[Nightdriver]

do you pay the full boat on each of these dates?

[NorthDallas40]

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

[Nightdriver]

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)

[NorthDallas40]

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!

[NorthDallas40]

And also guys - ALWAYS pay for the first date. I don't care what your (or her) philosophy is, but it's the polite thing to do and it's the #1 best way of never being accused of being a cheapskate.

[NorthDallas40]

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.

[NorthDallas40]

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.

[Nightdriver]

Nicola confirmed for Thursday and even gave the thumbs-up for an after-dinner activity I suggested.

Twister?!

Thanks for the updates. Those of us living vicariously through you appreciate them

[NorthDallas40]

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!