I had an incredible date last night with a 40-something! And we’re going to see each other again! The stars have finally aligned and pigs are flying.
Met on: Tinder
48 years old, self-employed entrepreneur, divorced, 1 kid
He drove an hour south to San Francisco from fire ravaged Healdsburg, arriving 10 minutes early. He sent me a text letting me know he’d been seated at an upstairs table in the microbrewery.
I saw the text after I had parked, then sent him a text letting him know I was on my way inside.
I saw him sitting at a table next to the railing as soon as I walked inside, then made my way upstairs. He looked exactly like his photos: cute, light brown hair, blue eyes, big smile. He stood up when he saw me at the top of the stairs; we gave each other a big bear hug. He’s tall – 6’5″.
We barely stopped talking to take a breath over the next 2 hours. We ordered lumpia to share (my first time having it – awesome!). I ordered a beer sampler; he ordered an IPA.
We finished those, then ordered another round of beer. I opted for the saisson this time; he ordered another IPA.
We had engaging banter. We were interested in each other and eagerly asked about an equal number of questions.
He’s been separated for 6 years, divorced for 4. He has a 10 year old son that lives with his mom in Miami for 9 months of the year… an alternative shared custody arrangement. This is ideal for me because it means our child custody schedules won’t clash for 9 months out of the year!
He’s recently gone back to school to study screenwriting.
I found out that he, too, is a car enthusiast. We bonded over that. However, he almost got up and walked out when I called rims “hub caps”. Haha. We had a good laugh over that.
He had a package to deliver to a client in nearby Noe Valley and asked if I’d like to join him. Of course! We got some bonus chit-chat in the car there and back.
He dropped me off at my car, where we had two very nice goodnight kisses. The first one was a little frenzied and passionate. The second one was slower and more sensuous. Mmm, I like!
I couldn’t stop smiling the entire way home.
I sent him a text when I got home at 11:30, telling him I had a really nice time and that I hoped he drove safely. Then I crashed.
When I woke up, there were a couple messages from him. He didn’t get home until almost 1 am because PG&E was repairing damaged power lines over the highway.
He said, “Lauren, I had a super fun time with you tonight! And thanks for joining me on my delivery run. If you’re free, would you like to have dinner with me up here in Healdsburg on Thursday? There are great restaurants here and they need a return to business as normal! What do you say – I know it’s tight notice.”
Wow, a 2nd date?! An actual 2nd date with a 40-something?? I couldn’t believe my eyes.
(And he said he couldn’t stop smiling on his drive home, either.)
Unfortunately, I already have plans on Thursday. I suggested other nights. Looks like it will be nearly impossible to schedule something within the enxt couple weeks due to my kid custody schedule and his school and work schedule. Ugh. But we will work something out soon!
If we can somehow manage to see each other on a regular basis and if he can keep up with my sexual appetite, this may be the beginning of something special. I’m excited!
I’ve received a few messages on Seeking Arrangement. I responded to one… from a sweet and respectful 59 year old doctor. He “unlocked” his photos – he was attractive and fit! What struck me was how humble he was.
His message, in full: “Your photo is happy and cute. Not sure you’d be interested but why not try. I think we may be a great match. I do like what you have written about connection and conversation. I seek chemistry, connection, mutual respect, and sensual pleasures indoors and outdoors. Above all I would like to think we can both like and be kind to one another. My level would be about $3k/month. Figure it’s better to get the fiduciary parameters out of the way.”
I liked his photos and he seemed like a sweet guy. I responded with, “I think we should meet in order to assess chemistry and compatibility, then go from there.”
We set tentative plans for a Saturday morning brunch date. (He won’t know what his weekend schedule is like until Friday.) He sent me the name of the place he’d like to meet on Saturday – an upscale cafe downtown.
This could be fun!
The most important thing is chemistry, obviously. If we have mutual chemistry, I intend to ask a lot of questions about his expectations. For example, how many times per month would he like to see each other? Will I attend events with him and/or meet his friends? Will we travel together? By the same token, he’ll need to know that I won’t ever be available at a moment’s notice.
You guys, my social calendar over the next few days is nuts. Tonight: First date (drinks) with a 31 year old Tinder dude. Tomorrow night: Date #4 with Surfer Dude. Friday night: First date (drinks) with a 47 year old Tinder dude. Saturday morning: Possible first date (brunch) with 59 year old Seeking Arrangement dude. Saturday late afternoon: Possible first date (not sure what yet!) with 32 year old Tinder dude. Saturday night: Dancing with Jill and another female coworker. Sunday morning: First date (coffee) with a 46 year old OkCupid dude.
You won’t believe this but as I was typing this post I received a text from Irish Spaniard… the guy I had one date with last May who sent me an unsolicited dick pic when I told him I was taking a break from dating soon afterward. I’m not going to respond.