How to Celebrate Valentine's Day with a Sorta Boyfriend

So, maybe you're kinda-sorta seeing a guy, but you haven't quite DTR-ed (our shorthand for "defined the relationship") yet. Sorry to be the bearer of bad news, but things may go from casual to complicated as Valentine's Day approaches—especially if you and your guy have different expectations for how you'd like to spend the holiday or for your budding relationship.

To help you make it through, we've outlined some tips to keep you sane.

1. Speak up
There's a ton of pressure on guys who are actually in relationships to go all out and impress their ladies, but the pressure on your maybe-not-sure boyfriend is far worse: If he does too little for you on VDay he risks making you think he's not that into you, and if he does too much he risks scaring you away or making you think that the relationship is farther along than it really is.

Our advice is to be frank about it: You and he both know that February 14th is approaching. Bringing up the holiday casually could be a good way to gauge how the dude feels about it (and perhaps just how romantic-minded he is), as well as give you some insight into his past relationships/experiences (which can be helpful). If you're really into him and would like to spend Valentine's Day together, you have to tell him so. Perhaps suggest hitting a bar together or going to a house party—something more low key than a $75/person prix-fixe meal. (Sidenote: You really should only subject yourselves to that soul-crumbling fate once you're in a stable relationship and can successfully weather having to wait for two hours to get a table even though you made reservations.)

If he tells you he already has plans or doesn't want to see you on that day—take note. Maybe you're not that into VDay and could care less, maybe he's not into it either, but his apprehension could be a sign that he'll never be ready to make you his Valentine.

2. Don't expect too much
Whether or not you decide to spend the holiday together, be realistic. We've been guilty of believing that VDay holds mystical powers that could transform even the most aloof of man into a rose-bearing Romeo—and we've learned the hard way that, no, it doesn't. If he's not your boyfriend, he doesn't have to give you anything—not even a daisy he picked on the side of the road. (But if he does, be thankful.)

Also, don't expect this to be the night that he asks you to be his girlfriend. While we think it's important that you and he have that conversation at some point (if you do in fact want to be in a relationship with him), remember that there's a lot of pressure on VDay and he may not want to go there.

3. Make your own plan.
If the guy won't commit to a plan or you're worried he might back out at the last minute (a potential red flag—if he's overly wary of spending VDay with you, he probably has some misgivings about ever making you his GF), then you should buck up and form a plan of your own.