Dating is hard. Equally hard is getting that date in the first place. To do that, you’ve got to find a way to put yourself out there and ask them out. Sure, it’s scary, but it’s better than doing nothing and always wondering, right?

Today, I’ve got a few questions about the early stages of dating; from flirting to first dates, it’s not easy to deal with possible rejection.

But for those who are new to the blog, Dear Dating Bitch is my modern day advice column. If you’re in need of some advice, go ahead and submit your questions here. And don’t worry – it’s always anonymous.

Now then, let’s get today’s letters, shall we?

*Note: Questions may be edited for length/clarity

Dear Dating B: Advice on Dating

Q: I have a customer at work I quite fancy and it seems to be mutual, but every time everything ends in just a quick chat. I don’t feel it’s very professional to ask them out, what would you do?

Customer Service Courtship

Dear Customer Service Courtship:

First of all, you sound adorable. It’s very rare that I get a letter as sweet as this one, so thank you for that.

But, onto your question. I wish you’d expanded a little more on why you think the attraction is mutual. Not that I’m doubting your judgement, but more context is always helpful. Especially since you go on to say that every interaction ends with a quick conversation. That leaves me to believe that one of two things is happening here.

One: this customer is just polite, friendly, and possibly a little bit flirty, but otherwise only sees you in a professional manner.

Two: this customer does like you but doesn’t want to take up too much of your time at work.

Either scenario is plausible. So, your job is to try and figure out which one it is. Next time they come to you, try and expand the conversation a bit. Ask them more about their day/weekend/job/likes/dislikes and see how they respond. Or, throw them a compliment. It doesn’t have to be overly forward or suggestive. A simple, “Wow, you look very nice today,” would probably go a long way.

Another option would be to ask another co-worker if they think this customer is into you. Getting another person’s perspective might help.

Finally (and this one is riskier), just ask them out! I’m not sure what field you’re in, but I personally don’t think asking someone out for coffee would be seen as unprofessional.

Q: How would you feel if your Tinder date was organizing another Tinder date in front of you?

Tinder Dating Horror Story

Dear Tinder Dating:

I’d probably feel a mixture of things, namely irritation, annoyance, and frustration. I’m sure a part of me would also feel embarrassed, maybe even insecure. I imagine that you’re feeling all of the above. And I can also imagine that your question was rooted in a desire for validation that your feelings are normal. Let me assure you, they are.

Now that I’ve gotten that out of the way, I’d rather give you advice on what you should feel, as I think it might be more helpful.

You could start by feeling relieved. As inconsiderate as they were, your date did you a huge favor. They showed you their true colors before you had a chance to develop any feelings for them. What a time saver that is!

Follow that with a healthy dose of amusement. Everyone has a good ‘bad date’ story to tell. And man, oh man, is this a good one. So, tell your friends about it and have a good laugh.

Related Read: 5 Red Flags on Tinder you Should Never Ignore

Q: I’ve been planning a third date with this girl, but she’s extremely unresponsive. I know she works a lot, but I haven’t heard from her in over a day. Then, when she does reply, she just “likes” my texts. I’m just really confused here. Should I be worried?

Third Date Limbo

Dear Third Date Limbo:

I’m not sure I’d go as far as to say “worried,” but I’d certainly be confused and even a little annoyed if I were you. Not everyone is permanently attached to their phone. And sure, she may be working a lot or have a lot going on in her life. But even the busiest of people can make time for a quick text. To go over a day without replying to someone who’s actively trying to make plans with you is just plain rude.

I think your real question, though, is on what to do now.

Assuming you still want to go on another date, my best advice would be to talk to her. Be straightforward and direct. You don’t need to be cruel or even outwardly irritated about it, but you should let her know how her behavior is impacting you.

If you already have a third date scheduled, I would say just wait until then. While on the date, you can mention her texting habits.

But, if you haven’t actually put anything concrete on the calendar, I think your next move would be to suggest a specific date. Are you free for dinner next Friday at 6pm? I was thinking X restaurant.

Hopefully, she will give you a definitive yes or no rather than just a ‘like,’ but if not, then, again, be direct. Sorry, was that a yes?

If the confusion continues, though, I have to be honest and say go ahead and cut your losses.

☆ ☆ ☆


Let me just say, as hard as dating is when you’re single, it’s all worth it when you find the right person. So, take that leap. Ask them out. Risk rejection. And keep your heart open.

What do you think of my advice this week? Let me know in the comments below!

As always, thanks for reading. If you’ve got questions of your own, make sure to send them to me here!


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  1. avatar

    Loved reading the answers to this week questions! Asking out people can be so daunting mostly if you are not certain of the other party, but as you said, it’s better take the plunge than regret it!

    1. avatar

      Absolutely! The worst they can say is ‘No thanks’

  2. avatar

    Some great advice to these problems! I think the first one sounds sweet too although I would be cautious depending on the industry this person is in!

    1. avatar

      Yes, I agree. It’s sometimes hard to give a proper answer when I don’t have as much information as I might like.

  3. avatar
    ellegracedeveson says:

    This is such a great read, thank you so much for sharing with us! It can be really scary asking someone out but sometimes you’ve just got to take the plunge and overcome that fear. It may be worthwhile in the end! I found todays post really interesting, an amazing read Xo

    Elle –

    1. avatar

      Aw, thank you! That’s always so nice to hear.

  4. avatar
    According to Chren says:

    Really great advice. Asking someone out can be scary. Another idea is to maybe see them outside of work without it being a date to see if there is any chemistry.

    1. avatar

      That’s another good idea – asking someone out for coffee doesn’t have to be a romantic thing, but you could also ask someone to a group happy hour/event that other people from work are going to so that it’s not inherently romantic.

  5. avatar

    Asking someone out is a bit scary. But, I agree that it’s better than doing nothing. It’s upsetting if you get rejected. However, at least you’ll know that it’s time for you to move on and find someone who can be a perfect match for you.

    1. avatar

      Absolutely! The worst that can happen is that they say no. And asking someone if they want to grab coffee is less intimidating anyway because if they say no, you haven’t professed your love for them or anything. You’ve simply asked to get coffee!

  6. avatar

    I know this may sound controversial but I have something to add to the last question. We need to get out more and talk in person. The kind of response you get when talking face to face will allay most of your fears. It’s hard to read people over the phone. Get out and ask for the date in person if possible.

    1. avatar

      Hmm… the problem with that is trying to “bump into” the person to ask them out in person feels a bit stalker-ish. Unless you happen to work or go to school with the person and do see them often, it’s best to ask for another date via phone/text and THEN try and talk to them on the date.

      1. avatar

        True. We just have to find the right balance.

  7. avatar

    I love reading questions and your advice on your blog! I think you were spot on with your advice! Thanks for sharing.

    1. avatar

      Aw, thank you! That’s always so nice to hear. I’m glad you enjoyed!

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30ish Lifestyle blogger, relationship "expert," and modern-day agony aunt.
Sometimes humorous, always honest.