Should I Lie To My Boyfriend About How Many Guys I've Slept With? Ask A Pro

Email your questions about living, loving and fucking to Head Pro at [email protected]. He’s also figuring out Instagram and can (and should) be followed at @betchesheadpro.

So, I’m gonna do a whole bunch of emails today, mostly because I’m a giant piece of shit who has plenty of time to tweet about president Trump’s saggy butt and french fry styles, but apparently not enough time to write anything for this website in the past, oh, month or so. I won’t apologize, but you do have my condolences for being deprived of my insightful content for so long. On to your emails:


So let me get straight to the point I randomly came across your site and I would like to say it’s very relatable to girls my age (I’m 22) so you see I’m dating this guy who in the beginning would like a lot of instagram hoochies pictures and I was ok with it you know boys will be boys but later as things got more serious it made me uncomfortable. My thinking was—does he want these types of girls? I’m comfortable in my own skin so I’m not an insecure person, but the fact that he was doing this non stop for the world to see made me start to feel insecure so I called him out on it and he’s stop with the liking not so much with the following the hoochies part that he doesn’t stop what I’m asking is am I overreacting with this?


Suddenly Insecure

Dear Suddenly Insecure,

Overreacting? Yes, probably. On the one hand it’s the social media equivalent of gawking at some hot babe passing by while you’re trying to talk about the new end tables you want from West Elm. On the other hand, he’s just poking a part of his screen in response to a post by someone he’ll never meet. Personally, I don’t understand a) why anyone follows non-celebrity IG models, and b) why anyone likes a post that isn’t either a funny meme or from an actual friend. There’s plenty of porn out there if he wants to see butts and boobs, and I’m not giving a stranger online validation for nothing in return. I think I’ve liked a post a total of like five times. Anyway, it’s fine, but it’s also fine if you tell him it’s kind of embarrassing (for him).

(You should like all my posts, though, because they are cool and good.)

Dearest Head Pro,

During my junior year of college (I will be going into my senior year this fall), I met a guy at work. I was working there before him so when he came in on his first day I was like ok damn you are very attractive. We worked in different areas so we didn’t communicate much, just made a lot of eye contact. We both ended up quitting, for other jobs, so towards the end of our employment the flirting went 0-100 real quick. Being a stupid betch, I told probably every girl and their mom in the office I thought he was the hottest thing since Matthew McConaughey. Maybe it got around, maybe it didn’t… (probably did). Regardless, on his last day he gave me a note right before I was about to leave for the day that said: Text me sometime, with his number, name and a fucking smiley face.

Long story short, we start texting the next day, hang out for the first time with other friends, and I (accidentally) got drunk off bottomless mimosas. So at the end of that day we shared our first kiss. Pretty romantic, I know. We got to hanging out, and things are going great. We decided to take things slow and it is obvious we both like each other.

This was 3 months ago. We’re still talking every day and I even brought him to my friends wedding as my date. All my friends really like him, and great cause so do I. Until he starts texting girls the entire time we’re at the wedding. I know I’m not the only girl he is talking to, which is whatever since we agreed to take things slow and since I’m not only just talking to him, but the gesture was a little rude. He constantly is upset over his ex and will go out of his way to text me and tell me that!!

I’ve started to distance myself, and I think he’s noticed, but why does he just want to text all day and night? Texts me back right away even when I send 3 texts a day, but barely wants to see me. We’ve hooked up a little, but have never had sex. So we’ve surpassed the just friends stage. Why doesn’t he make an effort to see me or progress things with me when it is obvious he likes me? We live an hour away when I’m home, which isn’t that far if he made an effort and I’m willing to do the same. HELP

Needs Brutal Honesty

Are You Still Texting Bitches

Dear Needs Brutal Honesty,

Nah, fuck this. WAY too much hassle if you’re not even getting laid. If I’m talking to someone constantly for three months and not even getting regular BJs out of it, that person had better be my parole officer or something. You’re right that texting girls at the wedding and/or about his ex is rude as shit, though I think I should point out that “occasionally getting to second base while he talks to other girls” is not most people’s definition of “taking it slow.” Stop taking rapid text responses as a sign of interest; it is literally the cheapest and easiest thing a guy can do (short of liking your Insta posts). Move on, this guy sucks.

Dear Head Pro,

About a year ago I broke up with my ex due to him cheating. He’s now in a serious relationship with the girl he cheated on me with, and I’ve heard they live together now. While the breakup sucked, I’ve moved on from him, dated other people, and he and I do not stay in contact.

Recently, he’s been texting me asking to see me, to get drinks, catch up, etc. I’m not sure what to think of this, obviously he’s in a serious relationship (see: living together) and we didn’t stay friends, so what would he want from me?

Do guys ever just want to “catch up” with their exes, or should I assume there is an alliterative motive (aka hooking up)?

Over it (kind of)

Dear Over It, 

I dunno about alliterative, but there’s definitely an ulterior motive at work. I’ve caught up with exes on occasion, but it’s not something I actively pursue—if I see one while I’m out, that’s fine and cool. But given his past transgressions and his persistence, there’s a solid chance he’s getting bored with his current situation. I also don’t believe you can’t be so naive as to not realize this, and just wanted to hear from someone else that, yes, your ex still has something in the tank for you. Do with that information what you will, probably something bad and dumb.

Dear Head Pro,

About seven years ago, I had an on-again off-again situation with a fuckboy in high school. We ended up going to the same place for undergrad and continued our toxic spiral until I called it quits after 2.5 years of being done with his shit. I’ll save you the details of the nature of our relationship, but since we never actually dated and he was an asshole, I didn’t feel the need to have a breakup conversation and just cut him out of my life, cold turkey.

…or so I thought. Fast forward to over 4 years after I stopped talking to him, and he is still trying to reconnect with me. A few months after I ghosted him, I would receive several calls, texts, and even one facetime request from him every few months over the next year. Since then it’s been Facebook and Instagram friend requests that I used to just reject, but now have blocked him since they didn’t stop after being denied over and over. Along with those came message requests (he can’t message me directly since I won’t friend him) that have ranged from “yo we good?” to “hi it’s been while, just wondering how you’ve been doing” to “sup hoezilla.” One time he even Facebook messaged my best friend asking about me, and when she ignored it, he wrote on her wall begging her to respond to his message.

All of this was obviously concerning, but I’m asking you for help now because he recently tried to add me on LinkedIn. My privacy settings on my other social media accounts are high so he can’t see anything, but my LinkedIn is public for career purposes. Even if I deny his request, he can now look me up at any time and know where I am and where I work. I really hate that idea, but I don’t want to have to change my LinkedIn settings and have it affect my career because of a dumb guy and his unsolicited and unwanted attention.

Please HP, I could really use some advice on dealing with this guy. My boyfriend thinks I should just respond and tell him to beat it, but I’m scared it will encourage him, like when you give cat callers attention.

– Here’s hoping you read this before he finds me!

Yikes Donald Glover

Dear Here’s Hoping, 

Uhhhh little late on this one, but here’s hoping you’re still alive? Anyway, while his behavior is annoying, it doesn’t sound to me (a non-expert in this field, mind you) like it’s threatening or escalating. Like, he’s not trying to see you in person, and his attempts to communicate haven’t gotten threatening or more severe. I think, given how long you were involved with him, it’s probably ok to respond to something and tell him to buzz off. Worst case scenario, you just block him again if he doesn’t get it.

As for LinkedIn, I think you’re taking it a little seriously. It’s a useful tool, but it’s also dumb as hell. You’re not going to miss out on any career opportunities if you make your shit fully private. Hell, I didn’t think you could do that, and I might now that you mention it.

Hi Head Pro,

I’ll get right to the point—I lied to my boyfriend about how many guys I’ve slept with, and the guilt is tearing me up and I don’t know if I should confess.

He asked the question when we were only dating for a couple of months, and it took me by surprise. I told him 5 (real number is 9). I don’t even know why I lied about it, I just wasn’t expecting the question and was caught off guard.  Looking back, I should have asked him if he really wanted to know, or told him it’s not relevant to our relationship and not given him any answer.

We’ve been dating almost a year now, and I honestly wasn’t too bothered by the lie. I didn’t think he really cared/wanted to know anyways, and it never came up again—until this past weekend. We got on the topic because of an issue our mutual friends were having, and my boyfriend flat-out asked me if I had lied to him about how many guys I had been with or anything similar. He said it wouldn’t change anything, but that it is a big deal to him, etc etc. I panicked. I defended the lie so well that I almost believed it myself.

I feel terrible about lying to him, because now I know it’s something that is important to him (even if it shouldn’t be) and we are a lot more serious now. I’m 26, he’s 28, we are about to move in together, have seriously discussed marriage/kids, and have a very strong, healthy relationship. I’ve never lied to him about anything before this.

I don’t feel like he would break up with me over this. It would hurt him, he would be upset that I lied, but then he would get over it. So I would feel better by confessing, but he would be hurt in the process.. which doesn’t sit well with me, but neither does getting more serious while we have secrets between us.

What do I do?

-Guilty Conscience

Dear Guilty Conscience, 

Ugh. Fucking dump him, that’s what you do. Like, really I have no patience for people like this anymore, even if I probably was this kind of fuckhead when I was younger. If you can’t dump him, just keep lying to him. Or even better, lie AGAIN and tell him the number is like 18 and see how he reacts. Maybe he’ll dump you, and you’ll have dodged a bullet. Like, it is seriously baffling to me that someone would bring this up not once, but twice, a whole fucking year after you started dating.

But really, just stick to it, and ask him why he doesn’t believe you, why he cares so much, etc. It’s not fair for him to pester you with a dumbfuck question he doesn’t need to know the answer to without answering a few himself.

Head Pro wants you to like his Instagrams, but he won’t like yours back. Email him at [email protected], and follow him on both Twitter and Instagram at @betchesheadpro.