Since sex workers are real pros when it comes to dating, turning first & blind dates into repeat customers, we’ve been asking them to share their best dating tips. We began with dating safety tips, covered making a good first impression, dished on dealing with dating jitters, exposed the secrets of how to get and keep those conversations going, addressed dealing with dating mistakes, and now we’re talking about what to do when that date is, well, a dog.
Let’s say the date is absolutely not going well for you; how do you handle it?
“Alice” (an anonymous sex worker with 17 years experience in erotic services, seven of them as a sex worker rights activist):
There are simply too many enjoyable people out there to waste time trying to enjoy someone you can’t.
I assess: Is this going poorly because we are in a place I don’t like, or is this person really the problem, or am I just not in the mood for this right now?
If the date is really just not compatible with me, I decide how gracefully I want to exit, and then I do it. Then I listen to loud music and tell myself I did the right thing, even if it was socially very scary for me. Ending a date early seems really hard, until you’ve done it, and realize how much better you can feel, and how quickly!
Angela St. Lawrence (erotic fetish phone sex operator):
If the guy’s a dick, I have no problem telling him so and leaving. But if he’s just boring or awkward, or there’s no chemistry, I’ll usually stick it out. Things could actually change during the course of the date, and if not, I’ve at least spared his feelings.
Addy Finch (an escort specializing in transgender/transsexual companionship):
First off, never hard schedule a time that you’re going to meet someone until; always leave yourself the option of going home early. This means not going to plays or movies or concerts. Again, transport yourself to your date.
Wrap up whatever you’re doing, finish your drink, or have your food boxed up. Let your date know that you have an engagement you need to get to and that you need to leave shortly. I normally check a clock with an, “Oh, gosh, that was quick. I’m supposed to meet up with a friend who’s in town.”
Whatever your excuse is, don’t allow for wiggle room on staying a little later. If they ask about getting together again, I tend to be courteous and let them know I’ll be in touch when my schedule’s clear. Unfortunately for them, there will always be something, even time alone, that’s more important.
Holly (an independent escort, sometimes brothel worker):
I always give myself an out… So I might go meet them at a bar, because I’m driving I can only have 2 drinks and then I have to go. If the date is bad, I will have the 2 drinks and then leave, thanking for the nice and time and tell them I will be in touch!
Claire Keeler (full service independent sex worker & award winning, published photographer working on a photographic essay called Whoretography):
Name the game and just say it the way that it is, “Look this is not going well,” a polite smile and exit stage left.
DiQld (a BBW MILF escort):
Thank them for a nice evening and wish them well in the future.
Kaylee Pond (geek culture and cosplay cam girl):
If I’m really not enjoying myself, I would probably still do my best to stick it out and give them a fair shot. If I’ve taken my own advice and met somewhere non-committal like a coffee shop then I should have a polite “out” fairly quickly. Once coffee is done I can just say that I have to go, thank them for the date, and say it was nice meeting them! I would avoid lying or acting like there will be another date if you know that there won’t be.
Goddess Audrey Rae (clip girl, occasional PSO and camgirl, specializing in Femdom and fetish):
I’m a big fan of the fake phone call. Both for safety issues and just to get yourself out of a situation you don’t want to be in anymore! If you really need to stick around for whatever reason, then try to save face as much as possible until you have an excuse to leave.
Secondhand Rose (a former escort, presently offering custom erotica and virtual companionship via text and telephone):
Be honest about it. Not only does that help avoid misunderstandings (and those repeated requests for dates), but sometimes it creates magic…
One time, I was on a date with a man I met on the Internet. We had great chemistry chatting there, and on the phone; but when we were sitting together at the restaurant bar, having drinks, the chemistry was just not there. It wasn’t even awkward and boring small talk — conversing was like pulling teeth! The thought of progressing to a table to eat with this man was an anathema to me. So I turned to him and said, “This isn’t going well, is it; let’s pass on dinner.” It was more of a statement than a question, but he agreed he felt the same. We decided to end the date — but a funny thing happened as we walked out the door…
We began talking about how awkward it was, how you never knew how things would be in person even if you thought you had great conversations online and on the phone, and suddenly we were laughing and dishing and voila!
We sat in the parking lot, sharing a beautiful summer’s night until the sun came up — and even then, we didn’t want to part. That date may have began as a “bad date”, but it led to a wonderful, committed, lovely, long-term relationship.
A Slip Of A Girl (phone sex operator, specializing in lingerie fetish, crossdressing, and sissification):
I usually try to make the most of it. Unless there is something creepy or unsafe, then I leave taking every safety precaution I can.
Typically, if I’ve had such a bad time that I do not to want another date, they are feeling the same way. But if they should call and ask for another date, I’ll politely but firmly decline so as to make it clear that I am not interested. It saves everyone’s time, patience, and feelings, really.