Ask dapperQ: Dating + Sex + Relationship Advice with Robin Cloud

*Feature image via Fozzie 320 Flickr

Dear Robin,

Two weeks ago I met an amazing woman on We met for tea/coffee on the first date, then had a nightcap two days later, where we made out in her apartment and cuddled till 5am. In my eyes she’s my dream girl: classic beauty, sophisticated, brilliant and beautiful. She totally checks off many of the ‘boxes’ that I’m looking for.

The thing is that this girl got scared and said I was intense a few days later (through text). She thought we were misunderstanding each other; I believe it was because we only were texting. I just met her today for coffee/tea and we spent 4 hours together (3rd meet up). It was amazing. I think we connected on a level that we should’ve been connecting with all along. No more weirdness or misunderstandings. To take the stress and pressure of dating out, I told her that I’d be ok as friends. All she does is smile and then she made a comment that “since the pressure is off, it makes everything a bit more intriguing.”

My question is: I don’t want to mess things up. I really like her and I want more. I just turned 30 and am looking for something serious, she is too (She’ll be 29 next month). We spent two hours in a retail store taking about decorating her room and she wants me to come over during the weekend to help her paint, etc. What do I do? I know I need to play it cool, but if I like her should I torture myself more by hanging out with her? I want to ask her if I have a shot but that might turn her off again.

Any suggestions???




Dear KF,

Oh the classic “Come here, but wait that’s too close!” First off, it doesn’t sound like you have done anything wrong to appear “too intense.” I mean making out and snuggling sounds pretty par for the course. Did something happened to appear “intense?”

In this day and age, everyone is texting like they have lost the ability to speak and I know it’s convenient. But, when you are just getting to know someone, you are still learning how to read their tone, and so miscommunication is bound to happen. Don’t schedule dates or discuss heartfelt emotions via text! Pick up that phone and call. Dag! So, there’s that.

If you like the girl, which it sounds like you clearly do, I would just let her know that you are enjoying getting to know her and are open to talking about how she would like to spend time together. Do not, and I repeat, do not continue to pretend that you don’t have a few bubbling feelings when you clearly do. It’s unfair to you and to her. Look, you have every right to like someone and want to spend time with them. That’s how dating works. If she is uncomfortable “dating” and can’t give you reasons why, then maybe she’s truly not your ‘dream’ girl, unless your dream girl is one who is more intrigued by being friends with no pressure benefits.



Dear Robin,

I am 28 year old masculine-of-center genderqueer person who is currently involved in my first poly relationship. The woman who has a primary partner and, while they have discussed being poly for several years, this is the first serious relationship my girlfriend has been involved in outside the primary relationship. My girlfriend and I have been dating for the last 4 months and the relationship is going very well. I have become increasingly involved in her family (she and her partner have a young child) and the three of us have discussed the possibility of me becoming a primary partner at some point in the future.  With this said, I often struggle in knowing how to supportive towards the primary relationship between my girlfriend and her partner. I often feel guilt about how well the relationship between my girlfriend and myself is going and I am afraid that I am taking away from her relationship between my girlfriend and her partner. I like my girlfriend’s partner and I want her to feel supported. I am unsure of how to discuss this with them, because it is their relationship and I don’t want to over step my bounds. I am hoping for advice on this particular situation, but generally, I am hoping to gain guidance on being a secondary partner. It seems that a lot of the information on being poly that I have found is geared towards opening up relationships as opposed to entering in as a new partner in an existing relationship dynamic.



Dear K,

Congrats on breaking into the world of Poly love. If your girlfriend and her partner have not directly expressed concern to you about the state of their/your relationship, where is this concern coming from? It sounds like you are the only one having a hard time with the situation. Explore what is behind your concerns. (Do you feel slightly undeserving? Do you not feel adequately supported? Are you struggling with self-criticism because your relationship doesn’t fit normative definitions?)  I would say that you should sit back and enjoy the new love that you are receiving and throw your guilt right out of the damn window! Everyone signed up for this party, so why waste your time feeling bad about it?

In regards to being supportive, I suggest that you sit your girlfriend down and have a little heart to heart. This is new for everyone and maybe she has some things that she would like to talk about as well.  Your girlfriend would be the best one to tell you what she/they might need instead of you trying to figure it out on your own. You are not a mind reader after all and you will not be over stepping your bounds by simply asking. Chile, find the courage!

Check out, “Opening Up: A Guide to Creating and Sustaining Open Relationships” by Tristin Taormino. Good luck!





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