I’ve now encountered a few men who say they want to date seriously but want to postpone meeting in-person until they feel they have built a sufficient rapport. I call this man “the penpal.” In one guy’s case, he wanted me to agree to being his girlfriend before we met. Another boasted he was the most romantic man in town but danced around meeting up. A third found my question about what a relationship with him looks like as an inorganic, outrageous question. Each of them hadn’t dated for years since the last partner either cheated or died. Two noted they were under psychiatric treatment, and for all I know, the other one could have been also.

The Mr. Penpal Type 

The shared trait among these profiles is that they seek a deep emotional connection over messaging before meeting. He wants your time and attention, but on his restrictive, virtual terms. He will paint a rosy picture of his current success and lifestyle involving multiple revenue streams, private chef, huge wine collection, and so on. These are fine things normally but in Mr. Penpal’s case, he’s trying to win you over. 

Pay attention to the jarring dualities in his words. He’ll say he’s living great but will mention nightmares of past trauma. He’ll say he sees a future taking trips together and sharing many moments but can’t bring himself to meet yet. In the last guy’s case, he flipped out when I shared what I thought an exclusive relationship looks like – home cooked meals, occasional date nights, and sleeping next to my partner. 

Identifying Mr. Penpal by His Red Flags

I first encountered Mr. Penpal last year. I was content with a penpal I came to regard platonically. Since then, I’ve gotten good at spotting him. The most recent one, I identified within 2 days. Here are his red flags:

He starts off by building trust in his stability. He builds this illusion because he’s not stable. He needs you to think he is to reel you into a virtual relationship. This buys him time, which he’ll phrase innocuously as getting acquainted. His back story: he’s been focused on building up his business the past few years and dated no or few women. He is successful. He can’t wait to have a long term partner. He is very interested in your day. He may make the “small ask” you stop talking to other guys – before you even meet.

He will tell you about a traumatic heartbreak. The guys I was unfortunate enough to cross paths with shared stories of losing loved ones associated with terrible accidents. This makes you feel bad for him so you talk to him some more, wasting your time while he gets the fulfillment everyone else gets through going out.   

He message bombs. This lets him stay on your mind since he doesn’t want to meet in-person for a very long time (if ever). After one of these messaging sessions, I got a “listening” call that originated from Stanford hospital (thank you caller ID), which makes sense if he was at the psychiatrist’s. Yes, that was extremely creepy. 

Left Swipe Mr. Penpal

Unless you are indeed looking for a penpal, this type of guy is the biggest time waste in all of dating land. He isn’t even capable of going on a real date despite his claims that he will arrange such a romantic date for you. Forget about forming a relationship! You can’t even validate his photos for starters. Likely, he’s not processed his issues – and his words reveal it. He sees a psychiatrist and uses present tense to describe his traumatic stress disorder. By his own words, he can’t be in a relationship in spite of wanting one.  

When his own words of intent don’t match up, there’s a problem and it’s not yours. Run if you find yourself talking to Mr. Penpal!