Ask Jess

You’ve been working too hard. Your life has become too serious. Your interactions with guys, of late, have been too fraught and heavy and intense.

What do you need? And how can you find it?

Easy.

Check out today’s tip HERE.

People LOVE to ask me what question I hear most often – during my travels, in my inbox, and catching up with my dear friends over wine and mac & cheese (we’re a classy bunch). Is it, How can I find a boyfriend?Or, Why hasn’t he asked me out on a date?How about, What tips do you have for building a strong, long-lasting relationship?

Nope.

The most common query I get is…drumroll please…What does this text message meeeeean?!

I get it. Human beings are confusing enough when they have unlimited characters, facial expressions and vocal nuances to play with. Transfer that all to a tiny screen with emoticons, sarcasm, misspellings and a good chance that someone has a beer in front of them, and it’s a wonder that we ever understand what each other is saying at all!

In the latest Ask Jess column, I take one step deeper into the jungles of techno-romance and address a reader who is mystified by a new dah guy’s presence on her Facebook page. How should she interpret his wall post? Is his “like” a sign of love? Is she now supposed to respond on his Facebook wall?

What does it all meeeean?!?!?!?!

You’re not the only Millennial in the post-dating world asking yourself this question. Put your mind at rest and finally get the answers you’ve been looking for HERE.

Ask Jess #15: What Does His Facebook Wall Post Meeeeean?!

Dear Jess,

I have a guy in my dah who has served as a combination Ego Booster/Accessory, and I’m fairly sure that I fill the same role in his.  Neither of us have expressed a particularly strong attraction to one another, but I definitely turn to him for much-needed compliments after a blow-off and we often accompany each other to parties or other social gatherings where one might not like to show up alone. In the wake of a very rough crumbling romance, it’s been nice to have someone to spend time with while I get my head straight to date (or non-date) again. At the end of the day, I’m pretty sure that we’re not interested in being a couple. But having someone around who is always up for dinner, a movie, commiseration, and mutual ego stroking is comforting.

Recently, I met him and a few of his buddies for drinks and brought along a female friend/co-worker.  The two hit it off, exchanged phone numbers (and a little saliva), and made plans to go out on a traditional date.

The next day, both of them asked me if I was okay with the situation. I answered honestly (mostly) that it was a little weird, but that overall, I didn’t have a problem with it.  I don’t want to root for it not to work out, because I want my friends to be happy. But I don’t know if I’m cheering for success either, because I very selfishly don’t want to lose my Ego Booster/Accessory.

In this messy world of new friendships and evolving connections, what do I do when dahs overlap? When my Ego Booster becomes her Boyfriend Prospect? How can we share dahs without resorting to the petty and stereotypical jealousy that so often destroys female friendships?

Sincerely,

Not Sure If I Should Be Jealous

Dear Jess,

I come to you seeking dah guidance. A girl recently came into my orbit, and I’m trying to figure out how to play it.

This girl is a friend-of-a-friend.  You could describe her as an Ego Booster…but I don’t really welcome her pursuit.  She asked me out, and while I didn’t really turn her down, I didn’t exactly say “yes” either.  And then I hear she’s telling people that I asked her out…?!?!

I decided to bite the bullet and be (sort of) honest.  I told her directly that I wasn’t looking to date right now, and that I didn’t want her to misinterpret the situation.  Her response seemed okay, and she brought up the option of hanging out as friends. I couldn’t say no to that, so I just told her that I was going to be really busy but would be in touch (wasn’t planning to actually get in touch, of course).

Since then, she’s texted me a few times asking to hang out.  Stuff like, “When are we hanging out?” and “Still busy? Want to go see a movie?” I try not to reply to every text, and when I do, I keep it polite yet non-committal.  But she keeps texting.

So…how do I make her go away?  I’m not into her, but I’m afraid of being harsh and burning a bridge with her and with our mutual friend.

Thanks,

Too Polite For My Own Good

Dear Jess,

This dude was really into me – he totally pursued me, invited me to a wedding, talked about future plans, etc. Then he started acting weird and broke up with me in a fit of panic, telling me that he was “still f**ked up” over a bad breakup from the past. After he emailed me a bunch of times, begging for forgiveness, I told him we could be friends.

Now he’s acting in a way that makes him seem like more than a casual friend – e-mailing me, doing really considerate things, coming to events filled with my friends who hate him, stalking my Facebook statuses and updates and posting old photos of us, offering suggestions for trips that I’m going on….

Do you think he realizes he’s made a mistake? Or is he just confused? Should I say something? Or should I get him drunk and let sh*t happen? Or should i let it go? I wish I could do that easily, but I really like him. I haven’t liked someone this much is a long time.

Help, Jess!

Friendly in Flux

Dear Jess,

So there is a gentleman in my dah who is a combination of The Prospect You’re Not Sure Is A Prospect and The Boyfriend Prospect (and occasionally The Unavailable Guy). I started out working with him, and then I drunkenly called him one night and told him to come out and be my down-and-dirty dance partner…

We hang out at least twice a week until 3 or 4 in the morning. He calls to tell me random tales he knows I’d be interested in, and he has made it a point to tell me every time he’s done (again) with a woman (which is for sure done this time).

My friends insist that he’s into me and that’s why we hang out until late so regularly. But what if he just likes my company? I’m notoriously excellent at “bro-ing down,” so I’m not sure if he’s awkward and can’t work up the courage to make a move, or if he just enjoys hanging out and being friends.

Bottom Line: I’m not sure what he wants.

Either way, I obviously enjoy his company and don’t want to f*ck up and make him uncomfortable. Oh, right, I’m also really proud.

WTF should I do?!

Fondly,

Trying Desperately to Make a Good Thing Better

Dear Jess,

I am just going to dive right in.

I went out on three dates this weekend. Two awful dates on Friday night, and one great date on Sunday. As a result of the two awful dates, I got a little overexcited on the good date – as did he.

I ended up sleeping with him. On the first date.

Can this be salvaged? We already made more plans, but I am skeptical. Can I still turn this into a relationship?

Love,
Overexcited Ollie