Confessions Of A Successful Over-40 Dater

I put absolutely everything out there, so I was incredibly relaxed by the time the dates came. Relaxed enough that I could be unapologetically me -- no more masks.
Publish date:
December 7, 2013
relationships, 40s, Dating, Sex,

Since moving to NYC 13 years ago, I’ve learned to avoid calling myself a success at anything. New Yorkers take success seriously.

There is always someone better, bigger, brighter at the next table or one door down from you. I remember once being brought to tears at a party because someone dared to call me a success. I had been invited to a party by a new friend and I arrived late and was introduced to the room (of vultures) as “This is Mata, my successful and funny new friend.” I had no idea what success she was speaking of and I laughed at the introduction because I knew it was completely false. I say all of this so that you understand that when I say I am a success at dating you know how carefully I have weighed the word success before using it.

For me success at dating means: great sex, tons of flattering contact, many attractive choices, and a general feeling that you are fantastic and in control of your romantic destiny. That is how I felt throughout my last 4 months of dating online. I went into it with two simple goals: have sex and start dating again. Both of those goals were met beyond what I could have imagined. During this dating experience I have been groped by many strangers, I have had sex with two men, I have received tons of sexts in the form of words and photos. I have gone to comedy shows, bars, on walks, to movies and have had someone make me dinner. I have made out passionately throughout Soho, held hands, laughed till I cried, had my nipples pinched and been given the best oral sex of my life.

I entered this experience with sub-zero expectations and that is one of the keys I believe to my success. I posted my online profile 4 months ago and immediately called my therapist to discuss seeing her twice as often in order to offset the pain and humiliation of online dating. At the time of posting my profile I had not had sex for 3 years and I was just coming out of one of the toughest times in my life. Things were just starting to get better for me and I was worried that online dating might throw me back into the fire pit of despair. So you can imagine my surprise when things immediately went the other way.

A few days after posting my profile, I had to travel out of town for a wedding. I decided to perfect my profile before leaving so I could relax while I was away and come back to many potential suitors. I worked very hard on the language and photos. By the time I finished, I sounded and looked near-perfect. The only thing left to do was answer the questions on the site. I went through and answered about half of them (close to 500). Many were very personal:

Would you have a threesome?

Me: Been there done that.

Would you allow your lover to spank you?

Me: Yes, please!

Do you enjoy giving blow jobs.

Me: Sure!

Have you ever done drugs?

Me: Yes, all of them.

Are you on this site to have sex?

Me: Absolutely!

I noticed on the way to the airport that I had gotten 4 new emails overnight. By the third day of the wedding I had received 30 emails. Right before leaving the wedding to go home, I confided to a fellow guest and friend that I was online dating. I told her I had received 40 emails in 4 days and about 200 “likes.” She was very encouraging and somehow the conversation moved to the questions I'd answered and she informed me that all my answers were displayed publicly unless I specified otherwise.

I had a 6-hour flight home without Internet access to think about all my private answers that had been read by countless men and by the time I was unpacking I had gotten to the “fuck it” stage. Which gets me to my next key for success: honesty. I did go back over some of the more explicit questions and change my answer to private to keep the creeps away. But I only did that with a few; the majority I left public. I also decided to go back night and re-edit my profile to make it equally honest. I mentioned that I had a tendency to sweat profusely, that I was hungry all the time, that I was a very competitive person, that I dyed my hair, that I lied about my age and that I had issues with claustrophobia.

I also changed my photos. I didn’t put up horrible photos of myself but I did change the images so that you could more accurately see my pros and cons. I took down a photo that was literally the best photo that had ever been taken of me...because in truth it really didn’t look like me. It was some trick of the lens that made me look superhumanly perfect. In its place, I put up a bikini shot that is shot from behind as I am walking away. The image is flattering but it is also very clear hat I have a big ass. It's a completely nice ass, but it's substantial enough that if you’re not into asses then I’m probably not for you. So now my whole profile was accurate and honest and I was sure that would end the stream of emails.

But the emails just kept pouring in. I was shocked. So I even took it a few steps further. I would tell my potential suitors in emails that I was 10 pounds heavier than what they saw on my profile. I told them I was currently an unemployed freelancer. I told them ... everything. And I think because I put everything out there I was so incredibly relaxed by the time the dates came up that I could actually enjoy myself. There was no mask that I was hiding behind. I was unapologetically me.

Of course not everyone was into the constant stream of non-stop confessional honesty. I had one guy who asked me what my dream date was so that he could make it happen for me. I answered him immediately because I knew the answer “I would like to go to a sports bar and eat chicken wings and drink beer.” I never heard from him again. Re-reading our email exchange later I can now see that he was alluding to something romantic and that I was soo excited to tell the truth that I didn’t pick that up. Another date that I was arranging over email asked me what film I wanted to see and I said “12 Years a Slave” and never heard from him again. Too Heavy? I told another man that he looked like “he could be my brother” and that I thought that was “hot”...never heard from him again either.

In total I have been out with 10 men over a 4 month period of time. All of the men were very attractive (except for one). I will most likely stay in contact with about 3 of them moving forward. I enjoyed each and every date thoroughly-even when there were not enough sparks to create a need for a second date. Its been great spending time with men. It struck me over again and over again throughout these dates just how much I was enjoying male companionship and it made me realize how badly I had been lacking in it. I also learned about things that I had been ignorant about previously. Information and facts about science, music, cooking and medicine but also about different kinks and sexual preferences. I remember going home after a few of my dates and googling sexual terms they had mentioned. “What is a Cuckold?”“What is Good pain?”An unexpected outcome of these dates was an education.

At one point during the four months, I was dating three different younger men at one time (for an overlapping time period that was about 4 weeks). Each of them knowing about the other two. I have never been romantically happier than during the time I was dating these three men at the sametime. Sex with one of them was exceptional and I was with him the longest-ten weeks, but the brains and conversations with the other were fantastic and I was with him for about two months, and the drunken hang outs with the third were soo much fun but only lasted about a month. During this time of man-overlap I was fielding emails and texts all day-booking the week carefully so that I would be fresh for each of them. It was a thrilling and completely selfish time period that I ended when each of the relationships started having the multiple layers and complexities of a “real” relationship and me realizing that I was not interested in doing that with any of them. So I ended it with the three of them...or more accurately I just stopped contacting them.

The truth is I don’t think any of them were crushed when I stopped contacting them. Not that I wasn’t special to any of them-I think they all liked me- but not enough for it bother them when it ended. The one common factor between the three of them was that they were all long term online daters. Each had been doing it for years. So I think they were well versed in having intimate but brief encounters with strangers. And I think there are pro’s and con’s to that. The pro is that they didn’t need a relationship to end in marriage in order for it to be deemed a success. And the con is that they had probably had a dozen similar fleeting romances and that in some ways I was nothing new.

After I ended my tripod relationship I thought a lot about what I could take to my next dating experience. The honesty that I had become comfortable with during the last 4 months would definitely need to come with me on my next adventure. But I decided I wanted to add more vulnerability to that. I am ready to not just date but also to be emotionally open to falling in love. So that is where I am currently. I’m thinking about trying to incorporate more “real time” dating where I just talk to people in social situations. I also think it would be interesting to meet through a matchmaker or to try more online dating sites that specialize in finding life partners and/or long term romances.

Would love to hear from you readers on recommendations for this next round of dating. Do you have matchmakers you can recommend? Or sites that you are really happy with? Please let me know.

Phase 1

4 months in.

Goal: To have sex and start dating again.

Goal achieved.

Pro: gained self-esteem, sex terminology education, sexual satisfaction, companionship and greater respect for the power of honesty.

Con: off-and-on head cold for over 4 weeks when dating the tripod-it just kept coming back around through the 4 of us.

Next goal is to combine “real life” dating with another form of cyber or matchmaking type of dating.

Goal: To find someone I’d like to date longer than a few months and possibly fall in love.