Best. First. Date. Ever.

You know those dreadful jokes men used to make… about putting a bag over a woman’s head? You know how we worry about that first date, how he’ll look, how we’ll look – especially if we only have an image or two exchanged online?

You know how we judge a book by its cover? Come on. We all do it.

A beautiful woman I know is beginning to see the signs of age, very slight, and she’s having difficulty facing it. She’s feeling insecure. She’s sensing an element of power slipping away. Worse, when she looks in the mirror, she doesn’t fully recognize the person who returns her gaze. Sound familiar?

I get it. I’ve been there. I’ll be there in stages for the rest of my life. After the age of 40, can’t we all say the same?

Personally, the sadness of it to affects me more or less – depending on how full and busy my life is at the time. That bag over my head?

Some days I want it for myself. Most of the time, that isn’t the case. But there are a few circumstances in which it might be helpful.

Aging and the Dating Market

Many women feel at odds with their appearance when other aspects of daily life are unstable. Or, if in the dating market, we may feel increasingly shut out by men our own age – especially when online dating seems like the only option and we’re left to decide whether or not to lie about how old we really are.

When I recall my years of Internet encounters, there were some wonderful dates, a few friendships made in the process, one or two lovely relationships that were relatively short-lived, and plenty of funny stories. I eventually came to the conclusion that Match and its alternatives were no longer a viable means for me to meet men. Not in this country, anyway. And not men I might be interested in – of my own age or younger.

And yes, I’m “for” dating and relationships with younger men. For me, that meant five years, eight years, possibly ten. If you want to and you can, why not? If they’re a better fit in terms of energy, libido, stage of life and pursuing common interests, I say go for it – whatever works, whatever you find mutually sexy, whatever is mutually satisfying.

Online Dating – Scary Proposition?

In general, dating at midlife can be daunting. Dating at any age is, yet it’s harder to dive back in after going it solo for years, after a marriage has ended, and when we’re rediscovering ourselves – including the aging process. It’s a scary proposition.

Is online dating scarier than a fix-up?

I’d say it’s a toss up.

And if you tell the truth about your age (as a woman), once you pass 45, online dating in this country is more challenging. Demographics shift; 45 year old men seem to want 30-year-old women, not women their age. You’re likely to be approached by men 10+ years your senior – which may be problematic when you consider the differences in stage and energy between 50 and 60, just as an example.

Of course, it helps if you know what you really want in a relationship.

And if you don’t?

Figure it out. Not by checklist! Think about character traits and values and common interests. And do you truly plan on rock climbing and rollerblading? Do you seriously require someone 6′ tall or with a particular eye color and in a specific profession?

No, this isn’t another testament to the Nerdy Guy. But it’s a reminder to get real – about good people and yourself.

First Date Planning

If I had to offer advice for first date planning, purely from my own experience? If you’re interested in the possibility of a relationship and not just sex?

  • Talk first! Really talk! If the talking ain’t easy, forget it.
  • Pick a spot together – one that’s comfortable for you both. And safe.
  • Note the exits in case of need to beat a hasty (albeit polite) retreat.
  • Don’t agree to an activity you know you’ll dislike.
  • DO go for coffee, a drink, a quick bite at a familiar eatery where you’re relaxed and no one’s dropping a bundle in the process.
  • Consider a walkable spot near a bookstore or other interest-adjacent locations to encourage dialog and learn about the other person in the process.
  • Don’t get drunk! Not even close!
  • No matching tattoos on the first date. Ditto, the second.
  • No discussion of marriage, divorce, death, illnesses, bad exes, or felony arrests.
  • Get all that out of the way before meeting – facts only – and brief.

My Best First Date Ever

And then there was my own best first date ever… It was an old style fix-up, and not the result of any online preliminaries. I was able to Google the gentleman in question and I found little but a picture of him dressed as, well… an elf. My conclusion?

Any adult man who had the humor and confidence for that get-up was worth meeting.

The circumstances leading up to the fix-up were strangely ironic. I’d call it serendipity. And before we met, we had a long, meandering conversation by phone. It turns out we had a great deal in common, and I was genuinely looking forward to our first date.

That doesn’t mean I wasn’t nervous. I was.

That doesn’t mean I didn’t glance in the mirror and fret over the deepening lines and more than anything, the fatigue that is harder to wipe away or camouflage as the years stack up. And then I imagined how wonderful it would be if we could dispense with the worry over appearance – the softening neck, the extra 10 pounds, the muffin top, the strands of gray.

What if we focused on words, scent, tone of voice, even touch – rather than allowing sight to rule?

What if all first dates came with “Bags Optional,” as a means to get to know someone for who they are?

No, I’m not suggesting you put a bag over your head for your next first date, or require it of your companion. But I love the idea as a means to remind us where our focus should be if we’re interested in a relationship.

As for my date, the plan for a quick drink turned into seven hours of wine tasting and tapas and conversation in two languages. Yes, I said seven hours. The connection was uncanny, exhilarating, and delicious. I felt seen – inside – by a man capable of experiencing another person fully.

Now that’s sexy.

And no bags required.


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  1. says

    I agree with everything you’ve said. And, at age 58 I’ve had my share of delightful dates and amusing stories! I often share a similar lists of suggested do’s and don’t’s.
    I’ve just gone off Match and OkCupid as well. I will hope to meet someone in my daily activity or through good friends.

    • BigLittleWolf says

      My approach, Walker? Say “yes” to every possible friend of friend, in person casual meeting, etc… The old-fashioned way…

    • BigLittleWolf says

      Well, Kitch, I am now part of the Elf Support Team. I highly recommend elves. Wonderful future in it. Especially at holiday season.

  2. says

    Wait. What happened? You leave me hanging!?! Remember American Graffiti? Just before the credits came up, they showed what happened to each of the characters. Are you ever going to tell us, your readership, just what happened with such a great first date? Then again even axe murderers like tapas and since you’re still alive, maybe there wasn’t a second date. Whew. Now that was a close call. :-)

  3. Robert says

    If I were dating, I would be looking for someone my age plus or minus approximately five years. I would want someone who has been around long enough to have had the same life experiences as I have. One of your posters said it well a while back – that relationships the second time around are like a virus, you want someone who has had it, suffered, developed the antidote by becoming better and deeper, and knows how to identify and value someone who has traveled the same path.

    Perhaps I am an anomaly, but when I see someone with the lines and grayness, that is a qualifier, not a disqualifier. The real criteria would be hardness vs. softness. Someone who has grown cynical and private would be of no interest, someone reflective and vulnerable would be very attractive. I see women in the sixty-ish range (perhaps even older) range quite often who I consider purely beautiful. I know much of that is coming from the inside out, from them feeling free to be who they are, rather than what someone expects. They have found their own beauty, and it shows.

    I wouldn’t try to attract someone who would be attracted to a person trying to be someone else. That can’t and won’t work – that person is looking for a different type of person, someone not like you. Be the person that the person you really want would be attracted to.

  4. says

    I am so thankful that I don’t have to worry about dating, especially of the Internet variety.

    Best first date ever! Serendipity!

    Your concept is a good one; don’t let sight rule – focus on the important stuff and not on appearances – well, at least not entirely. But, a bag over your head can make it difficult to eat. And, you can’t tell if the other person is smiling at your brand of humor. Even so, a bag might make for an interesting date. No bags needed – much better :)

    My stepfather is ten years younger than my mother (and ten years older than me). I have wondered how or if that would affect them as they aged. They aren’t any different than any other couple, who are growing old together. Age is simply not a factor for them.

    New look for your blog – FABULOUS!

    • BigLittleWolf says

      :) OK, Robin. A bag with eye holes. (I knew someone would mention that.)

      Glad you like the new digs! (More tweaks to come.)

  5. says

    I also love the new look! Very modern, clean and attirant!
    And am glad that I did internet dating when I was younger–although I definitely stumbled on some older men that had lied about their age. No second date for them! And yes, I always give the first advice to talk first–key!!

  6. says

    We actually made contact on Match, although ordinarily I wouldn’t put much weight on that approach. She was “Serendipty Fran.” This was different, right away. We talked for hours on the phone the first two days, before we met. Think I’ve told this story before. Brief version is that we arranged to meet by the Swarthmore water tower (behind the campus) after work for a night hike in the woods. It started raining an hour before our hike. I called her to check that things were still on. Her reply “Be there or be square.” I was smitten (I know I have told this story here as well as any number of places). Much more, all on my blog.

    Interesting tidbit related to some material in your post, is that she did tell me later that she wondered if I had kept the schedule just to make her look like a wet mess and unattractive. That was surprising and something to think about at the time… I had never expected to hear that from her. Of course, in a moment she forgets all about that and is a very strong person, and even at the time it was more an intellectual thought than a deep worry or concern.

  7. says

    You’re being awfully coy about the outcome of said date! But whatever the outcome, your evening sounds like it was a lot of fun! I can’t even imagine being back in the dating game again.

  8. DaveysHouse says

    Well, we were introduced by a mutual friend and we “dated” on the phone and exchanged emails every day for 6 weeks. Once, after we met, he worried that one day I would wake up and think he was too old. I said “you know, all I need to know is this is the person I wanted to speak to every night for six weeks, and whatever package you come in is the package you come in”. And it really was like that :-).

    • BigLittleWolf says

      I love hearing this, DaveysHouse! Thank you for sharing this. We need these stories which are a very different reality from what we’re normally fed via the media.

  9. says

    I think the easiest first date isn’t a date at all. It’s just being around someone doing something you’re both interested in. I met Bill in a running club. In ours there are three men for every woman. Their does seem to be a big age divide – under 30, over 50 (probably because of the career/child thing in the middle). There are social occasions involved in most clubs that allow individuals to mix freely. I think your ideas for a first date are great, I’m just throwing in this idea.

    • BigLittleWolf says

      That’s a wonderful suggestion, Shelley. More than anything, meeting in a “natural” setting helps. (I wonder how many people do, still? At least, in their 20s or possibly 30s?)

  10. says

    My best first date ever was with a guy I met in college. We had class together, so we knew we had some things in common and it was just a fun, night where we hit it off right away.

    My current relationship began as a blind date and we were introduced by a mutual friend. The friend asked if he could give this man my number and I said sure. When the man called, he introduced himself and we talked just the basics (divorce, children, etc.) for about a half hour and agreed to meet for lunch. I knew the time would be limited and was comfortable with the restaurant where I had dined before. I loved knowing that my friend had known and trusted this man for years. That allowed me to trust him more easily and to know that what I saw and heard were real.

    We ‘lunched’ for about two hours and it went by very quickly. Our coversation was easy, I remembering smiling a lot and walking away feeling like I had just met a wonderful person. I didn’t know where things were headed, I just knew I liked it!

    On the visual side, apparently he had looked up FB photos of me, but I was completely unaware of how he might look! My first thoughts were that I liked his height, thought he had kind eyes and a big nose. I didn’t think he was drop-dead gorgous then, but I do now … I guess that just emphasizes how much feelings have to do with impression. At least they do for me.

  11. Findlay says

    My tip for going on a best first date is DON’T until you’re sure what you see is what you get by using the video chat feature on one of the most popular sites such as attracion(dot)com – you’ll save time, money and the embarrassment of having to spend time with someone you’d rather not spend time with!

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