dear sharideth: I’ve Never Been On A Date

Dear Sharideth,

Here’s the deal. I’m an almost-30-year-old woman, and with the exception of prom [which was strictly platonic], I’ve never been on a date. Most days, this doesn’t bother me. However, I do want to get married and have a family and obviously the first step in that direction is to actually interact with men. I promise that I do not fit your description of “Miss Insecurity”. When I’m with my friends (both male and female), I am my confident, funny, snarky self. The problem is when I’m actually interested in a guy, I steer clear. I don’t know why I do this. On a conscious level, I just think I don’t have a reason to go out of my way to talk to him and initiate a conversation. I’m sure there is something deeper going on, maybe it is insecurity, it’s just not my normal self. I would love some advice, some brutal honestly, or any combination of the two.


Runs Away From Boys She Likes

dear RAFBSL,

being .0000001% Native American gives me the authority to rename you Runs From Men.  being 99.9999999% someone who plays a relationship advice blogger on the internet, i will try to help you become Runs At Men.

okay, maybe not that, but you get my meaning.

my initial response to your question is “well, stop doing that”.

that’s not helpful, sharideth.

i know, voice in my head who sounds weirdly like Kim Kardashian, just give me a second!

you’ve got to stop “steering clear”.  you may as well be shouting “GET AWAY FROM ME!  I’M NOT INTERESTED!  HULK SMASH!”  guys are no good at reading signs, but they’re going to read avoidance as rejection every time.

that doesn’t mean you have to all of sudden become the aggressor.  here’s some suggestions:

1.  say hello – calm down!  i know this is completely off the rails!  or not.  if a guy is looking for an opening with you, you initiating a “hey, what’s up, Jake*?” will be all he needs.  use his name and acknowledge his presence, that’s all.  you don’t have to fully engage and go straight for the conversation kill.  just let him know you see him.  you can even keep walking.  maybe even should…

2.  group date – pick a guy you could potentially be into and invite him to something you and your friends are doing.  if you happen to organize the whole thing just so you can offer the invite, trust me, he’ll be none the wiser.

3.  go bold – i once got a guy to ask me out by saying, “my boyfriend and i just broke up, you can ask me out now.”  he didn’t even know my name.  that was a Wednesday.  by Friday he had my name and my number.  in your case, i’d go with something like, “you should probably ask me out.” then walk away.  the walk away is key.  gives him a chance to pull his eyes back into his head and pick his jaw up off the floor.  okay, so this one is pretty aggressive, but it’s also kinda fun, if only to watch his reaction.

moral of the blog?  NO AVOIDANCE.  it’s like telling a guy you’re going to hit him in the jugular with a poisoned blow dart if he comes near you.

what other things can our friend do to put herself out there?

*i assume all fantasy cute guys are named Jake.


9 comments on “dear sharideth: I’ve Never Been On A Date

  1. Jenn says:

    I would add widen your friendship circle a bit both male and female because they might open you up to new social and eventually dating opportunities. Since you say you’re comfortable in your own skin, I’d say embrace that, flirt a little in those group settings and see who becomes interested.

  2. MattyGFresh says:

    I like all of these, but I just have to ask how #2 is really any different from this one from the 26 signs that she’s secretly insane blog; “I invite you to a party I’m throwing. And then quickly invite 100 other people so you won’t suspect I singled you out.” – he’ll show if he finds out you invited someone he’s actually interested in.” 😀

    That said, I actually really like the group date idea, but I would suggest that you pick a place for all of you to go where you’re at your most confident so you don’t have any outside confidence distractions and can concentrate on working on the one area where you struggle.

    • Jenn says:

      2 is only marginally different in that I would say it should be done really intentionally – in that you invite someone who you want to see if they get along with you but also your friends but in a small but casual setting like if you do group games night or whatever. It has to have the appearance of a date-ish setting without the date part.

    • Jennwith2ns says:

      Matty–I had EXACTLY the same question in my head. I was just too lazy to look up the post for quotes.

  3. Lord Alvin says:

    I would be curious to see what kind of tweets and status updates are being broadcast. Often times people will post things like pictures on FB that seem funny or normal to them, but just look crazy to others. Like it or not, if someone is interested in you they will Google your name before they ask you out.

  4. asoulwalker says:

    Number two is true more often than it is not… so many times we would totally not know…

  5. Jake Rohde says:

    Yes, we are all named Jake.

  6. If it helps, you’re not the oldest person on this readership who’s never been on a date. I’m at 35 and counting. Being in the same category with me doesn’t make you normal, sadly, but at least it makes you not alone in the category. 😉

    I decided when I was 12 that I wasn’t going to date till I was actively searching for a wife. I also decided I wasn’t going to date anyone I already knew I wouldn’t marry. Doesn’t mean the first person I showed an interest in would be the one I’d marry, it just means I didn’t see any point to traveling a *known* dead end road. It’s a waste of her time and emotions as much as it is of mine. I’m analytical that way.

    One thing I would ask you is this: do you feel you’re worth marrying/ready to get married? Being comfortable in your own skin is not necessarily the same thing as considering yourself a good catch and feeling you’re at a place in your life that you’re ready to be a wife. If you don’t feel ready for marriage or don’t feel you’re a good catch, that can be an inhibitor to pursuing a relationship.

  7. Steph says:

    Haha, your #3 made me laugh. Wait, reverse… I so relate to RAFBSL, except I’m a few years older and have been in relationships (and thus on dates), but none in the past couple of years. I have hit a serious dry spell and wondered why (and I’m in a new “pool” of men, as I moved not too long ago). I thought it was a vibe I was giving off, but within the past month, 2 different people have told me that I give off a great vibe and am like a ball of sunshine. Who doesn’t want some sunshine in their life, right? :p A few years back when I was dating, I did try the #3, and it was a lot of fun. This fella and I had been flirting on a few different occasions, so I just said “When are you going to ask me out?” I had never done something like that before, and never since. Not sure why I haven’t tried it again, since we went out and had a great time. I think I reverted back to my “I’m worth being pursued, so I’m not going to ask myself out for him.” I have gotten better at #1 though and not running away from any guy who could be a “potential”, so that’s progress! 😀

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