On How to Speak Up and Reach Out [Dear DBN]

By Datebynumbers

Think for a moment about what you do when you want a new job.  You build an argument on your cover letter, you outline all your accolades on your resume, and you apply.  Maybe you apply several times before you get hired.  Maybe you apply once and think, “Fine.  You don’t want me, you don’t get to have me.”  But either way, you put yourself out there and ask for what you want.  Now how often have you done this in your love life?  Right, that’s what I thought.  Santa Claus ain’t real, sweetheart.  If you’ve got a wish list, you need to make it a to-do list before someone else goes after what you want.  This week, how to speak up and reach out in attempts to get what you want.

I think I need to go after what I want for once in my life. Letting boys come to me just is not working. I met this cute guy the other day. We’re both students, in a hospital. As of right now I haven’t really talked to him besides introducing myself. I want to make a “bold move” and let him know I’m interested, but I don’t want the whole hospital to know. Is there any way I can be bold, but subtle at the same time? I guess I’m asking how to flirt with him?

Why not just ask him if he’d like to grab lunch?  Or a drink after a long shift?  Flirting is great – but workplace flirting doesn’t always mean actual flirting – it’s actually a common source of relief and even the happiest of couples have harmless “work spouses.”  Best to make your intentions clear so he can make his availability clear.  Asking someone to grab a drink or coffee after a shift is a super easy way for him or her to say, “Dang, that sounds nice but I gotta get home to my girl/boyfriend.”  And yes, I recognize that just straight up asking someone out can be a big step in the Bold Moves category, but try to frame it in your head as asking a colleague to join you for lunch.  Nothing out of the norm about commiserating with a coworker over some food or, even better, some brews.

It’s very rare that women approach men, so capitalize on that.  Be that fresh breeze in his life.  As for subtlety… while I understand your desire to keep something in your place of employment hush-hush, I’ve found that hiding in plain sight has its perks.  You don’t have to hide anything if everyone thinks you’re best friends.  If I used emoticons, I would wink at you right now.

I’ve been casually but exclusively dating a guy for the better part of a year. He makes me very happy, but he frustrates me with his quarter life crisis. He’s torn between being single/adventurous and committed/responsible, which leaves me in the middle! I’m a no-pressure person and have been very patient with his issues (because everyone has something), but I don’t know what to do at this point. I don’t want to be backburnered, nor do I want to end this because it’s not officially official.

I hate to break this to you, but you need to make up your mind about what you want.  It sounds like for a better part of a year, he’s been the conductor of this relationship and you’ve been following his lead.  If you want a change, you need to be the one to ask for it.  And you need to go into this discussion like you’re going into trial, because if he’s gotten away with this for almost a year, he’s not going to see a viable reason to change. If you tell him that you’re no longer comfortable with this loosey-goosey stuff, be prepared for him to be like, “But you’ve been cool with it this whole time and I’m not seeing anyone else.”  He’s going to use logic on your emotions, but no one wins a case without making the jury feel something.  This is your opportunity.

Decide what you want and make your case, and know that it might not turn out how you want.  But remember, should you request to have an exclusive labeled relationship and he declines, and you go back anyways because it’s easy and a good time, then it’s unlikely he’ll ever commit because you just showed him he didn’t have to.

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