Why dating is a challenge for being frum

I’m not entirely sure why dating is a challenge for being frum, but here are some reasons.  It’s definitely not a comprehensive list, though.

1. As has been well-documented, the lack of affection and suppressed sexuality feels psychologically damaging, and it’s not the same to direct the need for affection towards women.  Infants need to be touched and held, and the need for touch doesn’t disappear when you grow up.  Some people manage to do without, but I felt like a complete human being again once I started hugging men again.   I once saw a tsniut lecture by a Modern Orthodox rabbi who said it was okay to shake hands as a greeting, but emphasized over and over how important it was for singles to avoid doing anything sexual/affectionate before marriage.  ”When I married my wife at age 21, I had never had any sexual contact with a woman.  It is hard, but it is not impossible.”  Those of us who are more than a decade older than he was when he got married, and who have no immediate prospects of getting married, raised our eyebrows.  What does he mean by “hard”?  It’s not hard to be shomer negiah for a few years; a few years plus a decade, that’s hard.  And, I would argue, unhealthy for some.  
2. Hosting shabbat meals can be really satisfying, but in the past couple of years while cleaning up afterwards, I feel even more lonely after the meals than I would have felt if I had never had them. Cleaning up after a large, happy group of people intensifies loneliness.  
3. Going to shul, I’m reminded that my age peers are mostly married or dating, and many singles are close to a decade younger than me.   Trying to meet new people while feeling lonely is always a bad idea:  you radiate desperation, especially to men.  In the past couple of years, when I went to singles’ events despite feeling lonely, I’ve had a few guys almost literally run away from me; I am guessing it was the apparent desperation because they don’t generally run away from me when I’m not feeling lonely.  
4. Davening reminds me of shul and the loneliness that I feel there, and also reminds me of how I have been inserting the same words in the davening for nearly 10 years, asking for a shidduch.  Obviously davening doesn’t come with guaranteed results, but it does start to feel a bit futile.  See the next reason as well.
5. Learning, being careful about mitzvot, or anything else having to do with the mesorah, makes me wonder if I will have anyone to convey the tradition to.  Yes yes, no one should say “I am a dried up tree” (Isaiah) chas v’shalom, and yes, there is a reason to be observant even if one does not have children, but so much is bound up in “you shall tell your child” and being a good Jew for children is such a motivator for so many Jews, frum or not.  Once you have even a small infant, I’m told that you want to keep mitzvot so that they grow up in an environment full of Torah even before they know what it is. 
6. The only part of my life where my efforts are consistently rewarded is my job; dating fails unpredictably (as I’ve especially been reminded lately), but if I finish a project, the project is mine forever.  Greater involvement in work leads to more close-calls with shabbat, more travel away, and more disconnection from the community.  
7. Around the time that I turned 29, dating frum guys started to get difficult because 29 is already considered old.   Since non-frum people did not yet consider 29 to be old, I started dating them as well.  I still prefer frum guys, but given a choice is between children and observance, there’s no question:  children win.  Obviously, that’s the wrong halachic decision, and the choice is not that stark, but I would rather have a less religious family than no family at all or even a smaller family.  When I started dating non-frum guys, I had some illusions about whether they would become religious and I also had no clue how secular dating works. Now I have no expectations that they would become religious and I’ve become just as comfortable with secular dates as religious dates.  (For a secular guy to date me takes particular dedication since they assume correctly that I wouldn’t sleep with them, while a secular girl would.)
8. When you’re dating someone who is a good candidate for marriage, there’s optimism, but after a long period when there are no realistic dates, only crazy or unintelligent ones, or ones 15 years older, it looks like there’s no realistic prospects for marriage.  There are three ways to look at a run of failed relationships:  it’s random, you’re doing something wrong, or there’s something wrong with you.  Random is okay, but the latter two are disturbing.  In theory, you can correct if you realize that you are doing something wrong, but scrutinizing everything is hardly positive.    
9. While feeling lonely on shabbat, especially while cleaning up from a meal, while everyone has gone to be with their spouses or boyfriends, it really does help to turn on the radio or call a friend in a similar position.  The first time I did this was almost unconscious.  I thought of the Orthodox Forum woman and laughed.  Electricity on shabbat is not the worst issur in the world, and when I’m feeling so lonely it seems worth it.  
10. Dating is full of rejection, which makes loneliness feel more intense.  Much of the rejection in dating is unfair or embarrassing, which makes it easy to feel bitter and self-absorbed, which makes it harder to be observant.  Sometimes I even regret having done the “right” thing: for instance, if I hesitate at another date, but decide to give them a chance, and then they turn me down in an embarrassing way; the previous relationship where I was apparently too trusting. 

So far, I’ve been able to come up with 10 reasons why being single and over 30 challenges my observance.  I am sure that there are others, but it’s nice to even have this list.  

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